Home Cart Sign in  
Chemical Structure| 67104-97-6 Chemical Structure| 67104-97-6
Chemical Structure| 67104-97-6

2-Methyl-1,2,5-thiadiazolidine 1,1-dioxide

CAS No.: 67104-97-6

4.5 *For Research Use Only !

Cat. No.: A155249 Purity: 95%

Change View

Size Price

US Stock

Global Stock

In Stock
100mg łËî¶ÊÊ Inquiry Inquiry
250mg łòʶÊÊ Inquiry Inquiry
1g łÇóʶÊÊ Inquiry Inquiry
5g łďË˶ÊÊ Inquiry Inquiry

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 100mg

    łËî¶ÊÊ

  • 250mg

    łòʶÊÊ

  • 1g

    łÇóʶÊÊ

  • 5g

    łďË˶ÊÊ

In Stock

- +

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support Online Technical Q&A
Product Citations

Alternative Products

Product Details of [ 67104-97-6 ]

CAS No. :67104-97-6
Formula : C3H8N2O2S
M.W : 136.17
SMILES Code : CN1CCNS1(=O)=O
MDL No. :MFCD04037145
InChI Key :SYFJRHFWDDLSJF-UHFFFAOYSA-N
Pubchem ID :10393280

Safety of [ 67104-97-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H320-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Calculated chemistry of [ 67104-97-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 0
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 36.91
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

57.79 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.28
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.99
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.91
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.98
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.67
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.66

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.06
Solubility 118.0 mg/ml ; 0.87 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

0.26
Solubility 249.0 mg/ml ; 1.83 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Highly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.1
Solubility 108.0 mg/ml ; 0.793 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.83 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.48

Application In Synthesis of [ 67104-97-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 67104-97-6 ]

[ 67104-97-6 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 67104-93-2 ]
  • [ 67104-97-6 ]
  • 2
  • [ 67104-97-6 ]
  • 3-<2-<N-<(tert-butyloxy)carbonyl>amino>ethyl>-5-<(trimethylammonium)methyl>-1H-indole iodide [ No CAS ]
  • [ 144432-51-9 ]
  • 4
  • [ 109-81-9 ]
  • [ 67104-97-6 ]
YieldReaction ConditionsOperation in experiment
52.3% With pyridine; imidosulfonic acid; for 3h;Reflux; N-methylethylendiamine (1.5 g, 20.8 mmol) and sulfuric diimide (2.0 g, 20.8 mmol) were added to a pyridinesolvent (20 mL), and refluxed, stirred, and heated for 3 hours. After the reaction was completed, toluene (5 mL) wasadded to the reactant, followed by concentration and extraction with ethyl acetate. An organic solvent layer was driedover MgSO4 and filtered to remove the solvent. A residue was purified by column chromatography (EtOAc) to obtain acompound 6a. White solid (52.3 %). Mp 80 to 82 C; 1H-NMR (CDCl3, 300 MHz) delta7.27 (s, 1H), 3.53-3.19 (m, 2H), 3.42-3.37 (m, 2H), 2.75 (s, 1H); 13C NMR (CDCl3, 75 MHz) delta 32.67, 39.64, 46.94; LC-MS: Predicted value calculated with respect to C3H8N2O2S m/z: 136. Measured value: 137(M+1)+.
28% With pyridine; SULFAMIDE; at 120℃; for 16h; Preparation 98 2-Methyl-1,2,5-thiadiazolidine-1,1-dioxide To a stirred mixture of N-methylethylenediamine (1.200 g, 16.2 mmol) in pyridine (20 mL) was added sulfamide (1.867 g, 19.4 mmol). The mixture was heated in an oil bath at 120 C. for 16 hrs. After cooling to room temperature, the mixture was concentrated and the residue was partitioned between ethyl acetate and saturated aqueous sodium chloride. The organic layer was washed with 1 N aqueous hydrochloric acid, saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated to afford a colorless oil (0.61 g, 28%). 1H NMR (300 MHz, CDCl3) delta 4.30 (br s, 1H), 3.53 (m, 2H), 3.40 (m, 2H), 2.76 (s, 3H).
16% With SULFAMIDE; In 1,4-dioxane; for 20h;Reflux; Step a) 2-Methyl-?.2.51thiadiazolidine 1.1 -dioxide (Acid-12a); N-Methylethylene diamine (1.02 ml, 11.6 mmol) in dioxane (4 ml) was added dropwise to sulphamide (1.12 g, 11.6 mmol) in dioxane (10 ml) over 2 h. The mixture was refluxed for 18 h, solvent evaporated and residue purified by flash chromatography using 3% MeOH in DCM as eluent which gave the title compound (259 mg, 16%) as a semisolid.
799.4 mg With pyridine; SULFAMIDE; at 120℃; for 24h;Inert atmosphere; To a solution of N1-methylethane-1,2-diamine (2.0 g, 27 mmol) in pyridine (30 mL) was added sulfuric diamide (3.10 g, 32.4 mmol). The reaction was heated at 120 C under nitrogen for 24 h. All solvents were removed in vacuo. The residue was partitioned between saturated NaCl (aq, 25 mL) and EtOAc (125 mL) and organic component was washed with IN HC1 (aq, 50 mL) and saturated NaCl (aq, 25 mL). The organic component was dried over MgS04, filtered, and concentrated in vacuo to afford the title compound as a yellow viscous oil (799.4 mg). The product was used without further purification. NMR (400 MHz, CDCh) delta 4.48 (br s, 1H), 3.59 - 3.45 (m, 2H), 3.44 - 3.33 (m, 2H), 2.75 (s, 3H).
2.7 g With pyridine; SULFAMIDE; at 100℃; for 16h; To a mixture of sulfamide (5 g, 52.1 mmol) in pyridine (120 mL) was added a solution of n-methylethylenediamine (3.85 g, 52.1 mmol) in pyridine (30 mL) at 100 C. The mixture was stirred at 100 C for 16 hours, and then concentrated under reduced pressure. The residue was purified by column chromatography to give intermediate 1-17 (2.7 g) as a colorless oil. 1H NMR (400 MHz, CDC13) delta 4.37 (brs, 1 H), 4.45-4.58 (m, 2 H), 3.34-3.42 (m, 2H), 2.76 (s, 3H).

  • 5
  • [ 67104-97-6 ]
  • [ 350-46-9 ]
  • [ 144432-71-3 ]
YieldReaction ConditionsOperation in experiment
2.61 g (68.7%) In N-methyl-acetamide; water; 1. 4-(1,1-dioxo-5-methyl-1,2,5-thiadiazolidine-2-yl)nitrobenzene To a solution of <strong>[67104-97-6]2-methyl-1,2,5-thiadiazolidine-1,1-dioxide</strong> (2.02 g, 14.8 mmol) in anhydrous dimethylformamide (30 ml) was added sodium hydride (60% dispersion in oil; 0.59 g) and the mixture was stirred at room temperature under nitrogen for 40 minutes. A solution of 1-fluoro-4-nitrobenzene (2.09 g, 14.8 mmol) in anhydrous dimethylformamide (15 ml) was added to the above solution and the mixture was refluxed for 1 hour. Water (200 ml) was added and products were extracted with ethyl acetate (2*150 ml), dried (MgSO4) and concentrated to an orange solid. Crystallisation from ethyl acetate (150 ml) afforded 2.61 g (68.7%) of the title compound as a pale orange solid; mp 155-163 C.; deltaH (250 MHz, DMSO-d6) 8.29 (2H, d, J=9.3 Hz, Ar--H), 7.34 (2H, d, J=9.3 Hz, Ar--H), 4.00 (2H, t, J=6.4 Hz, --CH2 --), 3.57 (2H, t, J=6.4 Hz, --CH2 --), 2.78 (3H, s, --CH3); m/z (EI) 257 (M+).
  • 6
  • [ 67104-97-6 ]
  • [ 144432-49-5 ]
  • [ 144432-51-9 ]
  • 7
  • [ 67104-97-6 ]
  • [ 158664-98-3 ]
  • [ 158664-99-4 ]
  • 8
  • [ 67104-97-6 ]
  • N-[2-(5-Hydroxymethyl-1H-indol-3-yl)-ethyl]-formamide [ No CAS ]
  • [ 144432-64-4 ]
  • 9
  • [ 67104-97-6 ]
  • [ 144432-50-8 ]
  • [ 144432-54-2 ]
  • 10
  • [ 67104-97-6 ]
  • [ 100-11-8 ]
  • [ 144432-52-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N-methyl-acetamide; 1. 5-Methyl- 2-(4-nitrobenzyl)-1,2,5-thiadiazolidine-1,1-dioxide To a stirred suspension of anhydrous potassium carbonate (14.49 g, 104.8 mmol) in anhydrous dimethylformamide (80 ml) was added dropwise over 4 minutes a solution of <strong>[67104-97-6]2-methyl-1,2,5-thiadiazolidine-1,1-dioxide</strong> (14 g, 102.8 mmol) in anhydrous dimethylformamide (40 ml), under nitrogen. After 5 minutes, solid 4-nitrobenzyl bromide (22.43 g, 103.8 mmol) was added in one portion and stirring was continued at room temperature for 5 hours. Water (200 ml) was added and products were extracted into ethyl acetate (3*150 ml). The combined organic phases were washed with brine (1*50 ml), dried (Na2 SO4) and concentrated. The crude residue was crystallized from ethyl acetate-hexane (70:30) to give 18.31 g (67%) of the title compound as pale yellow crystals. Purification of the mother liquors by flash chromatography (silica gel, hexane-ethyl acetate, 30:70) afforded a further 5.1 g (18.2%) of required product; mp 105-107 C.; deltaH (250 MHz, CDCl3) 8.22 (2H, d, J=8.7 Hz, Ar--H), 7.57 (2H, d, J=8.7 Hz, Ar--H), 4.32 (2H, s, Ar--CH2 --), 3.36--3.21 (4H, m, N--CH2 CH2 --N), 2.80 (3H, s, --NMe); m/z (CI) 270 (M+ -1).
  • 13
  • [ 67104-97-6 ]
  • [ 137934-48-6 ]
  • (2S,4S)-2-(5-methyl-1,1-dioxo[1,2,5]thiadiazolidin-2-ylmethyl)-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine [ No CAS ]
  • 14
  • [ 65018-90-8 ]
  • [ 67104-97-6 ]
  • trans-2,2-dimethyl-4-[1,1-dioxo-5-methyl-1,2,5-thiadiazolidin-2-yl)-3-hydroxy-2H-1-benzopyran-6-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; chloroform; dimethyl sulfoxide; mineral oil; EXAMPLE 25 To a solution of <strong>[67104-97-6]1,1-dioxo-2-methyl-1,2,5-thiadiazolidine</strong> (0.89 g) in dimethyl sulfoxide 22 ml) was added 60% sodium hydride (0.26 g) in mineral oil portionwise under water-cooling. The reaction mixture was stirred at ambient temperature for 30 minutes and thereto was added 3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-1-benzopyran-6-carbonitrile (0.88 g). The reaction mixture was stirred at ambient temperature for 2 days, poured into ice-water (65 g), extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was subjected to column chromatography on silica gel (45 g) and eluted with a mixture of methanol and chloroform (1:50). The fractions containing object compound were combined and concentrated under reduced pressure. The residue was recrystallized from ethanol to give white crystal of trans-2,2-dimethyl-4-[1,1-dioxo-5-methyl-1,2,5-thiadiazolidin-2-yl)-3-hydroxy-2H-1-benzopyran-6-carbonitrile (0.28 g). mp: 213 to 214 C. IR (Nujol): 3520, 2220, 1607, 1275 cm-1. NMR (DMSO-d6, delta): 1.17 (3H, s), 1.43 (3H, s), 2.67 (3H, s), 2.83-3.50 (4H, m), 3.64 (1H, dd, J=6, 10Hz), 4.44 (1H, d, J=10Hz), 5.80 (1H, d, J=6Hz), 6.92 (1H, d J=8Hz), 7.61 (1H, dd, J=2, 8Hz), 7.70 (1H, d, J=2Hz).
  • 15
  • [ 36282-26-5 ]
  • [ 67104-97-6 ]
  • [ 936364-14-6 ]
YieldReaction ConditionsOperation in experiment
48% With potassium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 9h; A high pressure reaction vessel containing 2-bromo-4-fluorobenzonitrile (0.250 g, 1.25 mmol), 2-(methyl)-1,2,5-thiadiazolidine 1,1-dioxide (0.204 g, 1.5 mmol), K2CO3 (0.242 g, 1.4 mmol) and xantphos (0.058 g, 0.1 mmol) in dioxane (6 mL) was degassed with argon for 15 min. Pd2dba3 (0.034 g, 0.08 mmol) was introduced and the reaction mixture was heated at 100 C. for 9 h. The mixture was cooled, diluted with dioxane, and then filtered through Celite. The resulting mixture was concentrated in vacuo and the residue was purified with a Biotage column chromatography system on silica gel with hexanes:ethyl acetate (7:3) gradient as the eluent to afford the title compound as a white solid (0.152 g, 48%): 1H NMR (400 MHz, CDCl3) delta 7.69 (2 H, dd, J=8.6, 5.8 Hz), 7.52 (2 H, dd, J=9.5, 2.4 Hz), 7.09 (2 H, ddd, J=8.7, 7.4, 2.4 Hz), 4.06 (3 H, t, J=6.4 Hz), 3.56 (3 H, t, J=6.6 Hz), 2.90 (3 H, s); LCMS (+ESI, M+H+) m/z 256.
  • 16
  • [ 369-34-6 ]
  • [ 67104-97-6 ]
  • [ 1092980-88-5 ]
  • 18
  • [ 1149733-95-8 ]
  • [ 67104-97-6 ]
  • C21H19FN6O4S [ No CAS ]
  • 19
  • (2S,4S)-2-Chlorocarbonyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester [ No CAS ]
  • [ 67104-97-6 ]
  • [ 1193318-27-2 ]
  • 20
  • [ 171408-73-4 ]
  • [ 67104-97-6 ]
  • [ 779330-88-0 ]
YieldReaction ConditionsOperation in experiment
Sodium hydride (0.128g, 60% disp. in oil) was added to a stirred solution of 2-methyl- 1,2, 5-thiadiazolidine 1, 1-dioxide (0.433g) in THF (10ml). DMF (10ml) was added and the mixture heated at 80C for 5min then a solution of the product from step (i) (0.8g) in DMF (SML) was added. The mixture was heated at 60C for 10MIN, poured into water (100ml), acidified with citric acid and extracted with ethylacetate. The organics were evaporated under reduced pressure and the residue purified by chromatography on silica eluting with diethylether, yield 0.58g. 1H NMR CDC13 : 8 8.50 (s, 1H), 4.05 (t, 2H), 3.45 (t, 2H), 2.87 (s, 3H), 2.58 (s, 3H). MS: APCI (+ve) 307/9
  • 21
  • [ 51760-21-5 ]
  • [ 67104-97-6 ]
  • [ 1221400-16-3 ]
YieldReaction ConditionsOperation in experiment
75% With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 105℃; for 2h;Inert atmosphere; Step b) 5-(5-Methyl-l,l-dioxo-llambda*6*-ri,2,51thiadiazolidin-2-yl)-isophthalic acid dimethyl ester (Acid- 12b^; Tris(dibenzylideneacetone)palladium (27 mg, 0.029 mmol) was added to a degassed mixture of 5-bromo-isophthalic acid dimethyl ester (159 mg, 0.583 mmol), 2-methyl-[l,2,5]thiadiazolidine 1,1 -dioxide (Acid- 12a) (79 mg, 0.583 mmol), Cs2CO3 (474 mg, 1.46 mmol) and Xantphos (50.6 mg, 0.0874 mmol) in dioxane (5 ml). The mixture was heated at 105 0C under N2 for 2 h, the solvent was evaporated and the residue purified by flash chromatography using 2% MeOH in DCM as eluent, which gave the title compound (143 mg, 75%) as a yellow solid.
  • 22
  • [ 1237802-34-4 ]
  • [ 67104-97-6 ]
  • [ 1237802-48-0 ]
  • 23
  • [ 1202923-32-7 ]
  • [ 67104-97-6 ]
  • [ 1202923-74-7 ]
  • 24
  • [ 1254300-84-9 ]
  • [ 67104-97-6 ]
  • [ 1254301-12-6 ]
YieldReaction ConditionsOperation in experiment
61% With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 80℃; for 6h; Compound prepared as set out in step 1 of the scheme for example 3.1H NMR (300 MHz, CDC13) delta 2.89 (s, 3H), 3.57(t, J= 6.6Hz, 2H), 3.89 (s, 3H), 4.37 (t, J = 6.3 Hz, 2H,), 5.34 (s, 2H), 7.32-7.42 (m, 3H), 7.48 (dd, J - 8.4,1.8 Hz, 2H), 7.97(d, J= 2.3 Hz, 1H), 8.98 (d, J= 1.8Hz, 1H)MS (ESI+) m/z 523 (M[Br79]+l), 525 (M[Br81]+l)
  • 25
  • [ 134307-72-5 ]
  • [ 67104-97-6 ]
  • [ 1261242-16-3 ]
YieldReaction ConditionsOperation in experiment
42.9% Under nitrogen atmosphere, the compound 6a (0.856 g, 6.26 mmol) was dissolved in 5 mL of anhydrous DMSO,and 60% NaH (0.282 g, 11.8 mmol) was slowly added dropwise at 0C. The temperature was raised to room temperature,and then the solution was stirred for 1 hour. 2-(((benzyloxy)carbonyl)amino)ethyl methane sulfonate (1.5 g, 5.83 mmol)was slowly added dropwise at 0 C, and then stirred at room temperature for 5 hours. After the reaction was completed,extraction was performed with ethyl acetate, and an organic solvent layer was dried over MgSO4. Filtration was performedto remove the solvent, and a residue was purified by column chromatography (EtOAc) to obtain a compound 7a (0.82 g). Sticky oil (42.9%). 1H-NMR (CDCl3, 300MHz) delta7.36-7.30 (m, 5H), 5.19 (bs, 1H), 5.10 (s, 2H), 3.46 (q, 2H, J = 5.9 Hz), 3.36-3.26 (m, 4H), 3.20 (t, 2H, J = 6.0 Hz). LC-MS: Predicted value calculated with respect to C13H19N3O4S m/z: 313. Measured value: 314(M+1)+.
  • 26
  • ((R)-2-hydroxymethyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-carbamic acid tert-butyl ester [ No CAS ]
  • [ 67104-97-6 ]
  • (R)-tert-butyl (2-((5-methyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)methyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 50℃; for 2h; Part 1 - Synthesis of (R)-tert-butyl (2-((5-methyl-l,l-dioxido-l,2,5-thiadiazolidin-2- yl)methyl)-3,4-dihydro-2H-benzo 6] [l,4]oxazin-6-yl)carbamate [0241 ] To a solution of (R)-ierf-butyl (2-(hydroxymethyl)-3 ,4-dihydro-2H- benzo[£][l ,4]oxazin-6-yl)carbamate (200 mg, 0.713 mmol), triphenylphosphine (187 mg, 0.713 mmol), 2-methyl-l ,2,5-thiadiazolidine 1 ,1 -dioxide (97 mg, 0.713 mmol), and toluene (3567 mu) was added diisopropyldiazodicarboxylate (146 mu, 0.749 mmol). The reaction was stirred at 50 C for two hours. The mixture was partitioned between ethyl acetate and saturated NaHC03. The organic layer was washed with brine, dried (MgS04), and concentrated. The residue was purified by MPLC eluting with a gradient of 0-100% ethyl acetate in hexanes to afford the title compound: LCMS (ESI) calculated for Ci7H27N405S (M+H)+: 399, Found: 399.
  • 27
  • [ 52131-82-5 ]
  • [ 67104-97-6 ]
  • C18H21N3O3S [ No CAS ]
  • 28
  • C24H19F2N3O3S [ No CAS ]
  • [ 67104-97-6 ]
  • C21H21F2N5O4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
9.3 mg With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 25℃; for 3h; To a mixture of Intermediate VN-29 (0.050 g, 0.11 mmol) and Intermediate VN-28.1 (0.016 g, 0.118 mmol) in acetonitrile (1 mL) was added DBU (0.018 mL, 0.12 mmol). The reaction mixture was stirred at -25 C for 3 h. The reaction was diluted with acetonitrile (1 mL) and purified via preparative HPLC (AcCN/water/NH40Ac) to afford the tittle compound (9.3 mg). LC-MS retention time = 1.579 min; m/z = 510.0 [M+H]+. (Column: Waters Acquity UPLC BEH CI 8, 2.1 x 50 mm, 1.7 muiotaeta particles; Mobile Phase A: 5:95 acetonitrile:water with 10 mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10 mM ammonium acetate; Temperature: 50 C; Gradient: 0- 100% B over 3 minutes, then a 0.75 minute hold at 100% B; Flow: 1.0 mL/min; Detection: UV at 220 nm).
  • 29
  • (S)-tert-butyl 3-((4-(2-((5-amino-2-methylnaphthalen-1-yl)oxy)pyridin-3-yl)pyrimidin-2-yl)amino)piperidine-1-carboxylate [ No CAS ]
  • [ 67104-97-6 ]
  • (S)-tert-butyl 3-((4-(2-((2-methyl-5-(5-methyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)naphthalen-1-yl)oxy)pyridin-3-yl)pyrimidin-2-yl)amino)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In acetonitrile; at 80℃; for 40h; To a solution of tert-butyl (3S)-3- [[4- [2- [(5 -iodo-2-methyl- 1 -naphthyl)oxy]-3 - pyridyl]pyrimidin-2-yl]amino]piperidine-1-carboxylate (150 mg, 0.24 mmol) in acetonitrile (2 mL) was added <strong>[67104-97-6]2-methyl-1,2,5-thiadiazolidine 1,1-dioxide</strong> (64.1 mg, 0.47 mmol), copper (I) iodide (22.4 mg, 0.12 mmol), N,N?-dimethyl-1,2-ethanediamine (20.7 mg, 0.24 mmol) and potassium carbonate (97.6 mg, 0.71 mmol) followed by stirring at 80 C for 40 h. After cooling, the mixture was filtered, concentrated and dissolved in ethyl acetate (50 mL) and subsequently washed with H20 (40 mL x 2). The organic phase was dried over anhydrous sodium sulfate and filtered and the filtrate was concentrated in vacuo and purified by prep-TLC (50% ethyl acetate in petroleum ether, Rf= 0.1) to yield 22 mg (15% yield) of the title compound as a white solid. LCMS (ESI) [M+Na]= 646.1.
  • 30
  • [ 39684-80-5 ]
  • [ 67104-97-6 ]
  • C10H21N3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; General procedure: To the mixture of the precursor 10(2.26 g, 10.1 mmol, 1.5 equiv) and tert-butyl 1,2,5-thiadiazolidine-2-carboxylate 1,1-dioxide (1.50 g, 6.75 mmol, 1.0 equiv) in dry DMF(10 mL), was added Cs2CO3 (6.60 g, 20.25 mmol, 3.0 equiv). Themixture was stirred at room temperature overnight, and thenextracted with ethyl acetate. The organic phase was washed withsaturated NaHCO3 and brine, dried over anhydrous Na2SO4, filteredand concentrated. The resulting residue was purified via silica gelchromatography to give 11a as colorless oil (1.96 g, 79%).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 67104-97-6 ]

Sulfamides

Chemical Structure| 137830-77-4

A183771 [137830-77-4]

2-Methyl-1,2,6-thiadiazinane 1,1-dioxide

Similarity: 0.79

Chemical Structure| 5823-51-8

A163184 [5823-51-8]

1,2,5-Thiadiazolidine 1,1-dioxide

Similarity: 0.79

Chemical Structure| 654073-32-2

A151397 [654073-32-2]

Azetidine-1-sulfonamide

Similarity: 0.78

Chemical Structure| 3984-14-3

A108448 [3984-14-3]

N,N-Dimethylsulfamide

Similarity: 0.67

Chemical Structure| 147962-41-2

A118075 [147962-41-2]

N-Propylsulfamide

Similarity: 0.64

Related Parent Nucleus of
[ 67104-97-6 ]

Thiadiazoles

Chemical Structure| 5823-51-8

A163184 [5823-51-8]

1,2,5-Thiadiazolidine 1,1-dioxide

Similarity: 0.79