65938-77-4|5-Methyl-2-pyridinesulfonamide| Ambeed

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Quality Control of [ 65938-77-4 ] Purity: 97% SDS Specification

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Product Details of [ 65938-77-4 ]

CAS No. :	65938-77-4
Formula :	C₆H₈N₂O₂S
M.W :	172.20
SMILES Code :	CC1=CN=C(C=C1)[S](=O)(=O)N
MDL No. :	MFCD00661363
InChI Key :	HXURYNQXMBRJLU-UHFFFAOYSA-N
Pubchem ID :	3614199

Safety of [ 65938-77-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 65938-77-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.17
Num. rotatable bonds	1
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	40.2
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	81.43 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.89
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.11
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.12
Log P_o/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.	-0.96
Log P_o/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	-0.06
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.22

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.31
Solubility	8.35 mg/ml ; 0.0485 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.	-1.38
Solubility	7.26 mg/ml ; 0.0421 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-1.97
Solubility	1.83 mg/ml ; 0.0106 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.	-7.27 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	1.0
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)	1.91

Application In Synthesis of [ 65938-77-4 ]

* 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 [ 65938-77-4 ]

[ 65938-77-4 ] Synthesis Path-Downstream 1~35

1
[ 292638-84-7 ]
[ 65938-77-4 ]
[ 796034-71-4 ]

References: [1]Journal of Organic Chemistry,2008,vol. 73,p. 2862 - 2870.
[2]Organic Letters,2004,vol. 6,p. 4109 - 4112.
[3]Journal of Organic Chemistry,2006,vol. 71,p. 5876 - 5880.
[4]Journal of Organic Chemistry,2008,vol. 73,p. 2862 - 2870.

2
[ 498-66-8 ]
[ 65938-77-4 ]
(1S,2R,4S,5R)-3-(5-Methyl-pyridine-2-sulfonyl)-3-aza-tricyclo[3.2.1.0^2,4]octane [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4109 - 4112.

3
[ 622-97-9 ]
[ 65938-77-4 ]
N-(5-methyl-2-pyridinesulfonyl)(4-methylphenyl)aziridine [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4109 - 4112.

4
[ 931-88-4 ]
[ 65938-77-4 ]
9-(5-methyl-pyridine-2-sulfonyl)-9-aza-bicyclo[6.1.0]nonane [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4109 - 4112.

5
[ 100-13-0 ]
[ 65938-77-4 ]
N-(5-methyl-2-pyridinesulfonyl)(4-nitrophenyl)aziridine [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4109 - 4112.

6
[ 873-66-5 ]
[ 65938-77-4 ]
trans-N-(5-methyl-2-pyridinesulfonyl)-2-methyl-3-phenylaziridine [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4109 - 4112.

7
[ 33143-29-2 ]
[ 65938-77-4 ]
2,2-dimethyl-1-(5-methyl-pyridine-2-sulfonyl)-1,1a,2,7b-tetrahydro-3-oxa-1-aza-cyclopropa[<i>a</i>]naphthalene-6-carbonitrile [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4109 - 4112.

8
[ 2039-82-9 ]
[ 65938-77-4 ]
N-(5-methyl-2-pyridinesulfonyl)(4-bromophenyl)aziridine [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4109 - 4112.

9
[ 2628-16-2 ]
[ 65938-77-4 ]
N-(5-methyl-2-pyridinesulfonyl)(4-acetyloxyphenyl)aziridine [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4109 - 4112.

10
[ 3240-34-4 ]
[ 65938-77-4 ]
[ 84494-81-5 ]
N-[2-(4-tert-butyldimethylsilyloxyphenyl)-2-(acetyloxy)ethyl](5-methyl-2-pyridine)sulfonamide [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4109 - 4112.

11
[ 766-90-5 ]
[ 65938-77-4 ]
trans-N-(5-methyl-2-pyridinesulfonyl)-2-methyl-3-phenylaziridine [ No CAS ]
cis-N-(5-methyl-2-pyridinesulfonyl)-2-methyl-3-phenylaziridine [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4109 - 4112.

12
[ 394-46-7 ]
[ 65938-77-4 ]
N-(5-methyl-2-pyridinesulfonyl)(2-fluorophenyl)aziridine [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4109 - 4112.

13
[ 827-54-3 ]
[ 65938-77-4 ]
5-methyl-2-[[2-(naphthalen-2-yl)aziridin-1-yl]sulfonyl]pyridine [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4109 - 4112.

14
[ 2039-86-3 ]
[ 65938-77-4 ]
N-(5-methyl-2-pyridinesulfonyl)(3-bromophenyl)aziridine [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4109 - 4112.

15
[ 2039-88-5 ]
[ 65938-77-4 ]
N-(5-methyl-2-pyridinesulfonyl)(2-bromophenyl)aziridine [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4109 - 4112.

16
[ 1193-82-4 ]
[ 65938-77-4 ]
N-(4-methyl-2-pyridinylsulfonyl)-S-methyl-S-phenylsulfoximine [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 4983 - 4985.
[2]Organic Letters,2006,vol. 8,p. 2349 - 2352.

17
[ 960008-45-1 ]
[ 65938-77-4 ]
(RS)-S-{4-[(5-bromo-4-[(R)-2-hydroxy-1,2-dimethylpropyl]amino}pyrimidin-2-yl)amino]phenyl}-S-methyl-N-[(5-methyl-2-pyridyl)sulphonyl]sulphimide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With iodosylbenzene;iron(III)-acetylacetonate; In acetonitrile; at 20℃; for 62h;Product distribution / selectivity;	300 mg (0.76 mmol) of (R)-3-[{5-bromo-2-(4-methylsulphanylphenylamino) pyrimidin-4-yl)}amino]-2-methylbutan-2-ol (compound 9.1), 192 mg (1.12 mmol) of 5-methyl- pyridine-2-sulphonamide, 265 mg (1.21 mmol) of iodosobenzene and 266 mg (0.76 mmol) of iron(III)acetylacetonate are weighed into a flask, and 8 ml of aceto-nitrile are added. The mixture is stirred at room temperature for 62 hours and then concentrated in a rotary evaporator. The remaining residue is purified by chromatography (dichloromethane/ethanol 8:2). 100 mg (0.18 mmol; yield: 23%) of the product are obtained.
10%	With [bis(acetoxy)iodo]benzene; magnesium oxide;dirhodium tetraacetate; In dichloromethane; at 20℃; for 19h;Product distribution / selectivity;	Alternatively, the final productproduct can be prepared in the following way: 300 mg (0.76 mmol) of (R)-3-[{5-bromo-2-(4-methylsulphanylphenylamino) pyrimidin-4-yl)}amino]-2-methylbutan-2-ol (compound 9.1), 260 mg (1.51 mmol) of <strong>[65938-77-4]5-methyl-pyridine-2-sulphonamide</strong>, 121 mg (3.00 mmol) of magnesium oxide, 374 mg (1.16 mmol) of iodobenzene diacetate and 33 mg (0.08 mmol) of rhodium(II) acetate dimer are weighed into a flask, and 10 ml of dichloromethane are added. The mixture is stirred at room temperature for 19 hours and then concentrated in a rotary evaporator. The remaining residue is purified by chromatography (dichloromethane/ethanol 9:1). 42 mg (0.08 mmol; yield: 10%) of the product are obtained. 1H-NMR (400 MHz, DMSO): 9.70 (s, 1H), 8.37 (br, 1H), 8.09 (s, 1H), 7.91 (m, 2H), 7.69 (m, 4H), 6.06 (d, 1H), 4.83 (s, 1H), 4.04 (m, 1H), 2.98 (s, 3H), 2.29 (s, 3H), 1.12 (m, 9H). MS: 567 (ES+)

References: [1]Patent: US2008/58358,2008,A1 .Location in patent: Page/Page column 26.
[2]Patent: US2008/58358,2008,A1 .Location in patent: Page/Page column 26.

18
[ 701-57-5 ]
[ 65938-77-4 ]
[ 960008-46-2 ]

Yield	Reaction Conditions	Operation in experiment
54%	With [bis(acetoxy)iodo]benzene; magnesium oxide;dirhodium tetraacetate; In dichloromethane; at 20℃; for 24h;	(RS)-S-Methyl-S-(4-nitrophenyl)-N-[(5-methyl-2-pyridyl)sulphonyl]sulphimide 879 mg (2.73 mmol) of iodosobenzene diacetate are added to a suspension of 300 mg (1.77 mmol) of 1-methylsulphanyl-4-nitrobenzene, 610 mg (3.55 mmol) of 5-methyl-2-pyridinesulphonamide, 285 mg (7.10 mmol) of magnesium oxide and 78 mg (0.18 mmol) of rhodium(II) acetate dimer in 12 ml of dichloromethane at room temperature. The mixture is stirred for 24 h and then concentrated. The resulting residue is purified by chromatography (dichloromethane/ethanol 95:5). 326 mg (0.96 mmol; yield: 54%) of the product are obtained. 1H-NMR (DMSO): 8.41 (m, 2H), 8.31 (m, 1H), 8.12 (m, 2H), 7.76 (m, 1H), 7.70 (m, 1H), 3.11 (s, 3H), 2.29 (s, 3H). MS: 340 (ES+).

References: [1]Patent: US2008/58358,2008,A1 .Location in patent: Page/Page column 33.

19
[ 65938-77-4 ]
[ 519033-28-4 ]
[ 959468-41-8 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 8847 - 8858.

20
[ 65938-77-4 ]
[ 796034-87-2 ]

References: [1]Organic Letters,2004,vol. 6,p. 4109 - 4112.

21
[ 65938-77-4 ]
N-(1-phenylpropyl)(5-methyl-2-pyridine)sulfonamide [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4109 - 4112.

22
phenyl 2-[4-(2-ethyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethylcarbamate [ No CAS ]
[ 65938-77-4 ]
N-[({2-[4-(2-ethyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethyl}amino)carbonyl]-5-methyl-2-pyridinesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20℃;	STEP 2. N-[({2-[4-(2-ethyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethyl}amino)carbonyl]-<strong>[65938-77-4]5-methyl-2-pyridinesulfonamide</strong> A mixture of phenyl 2-[4-(2-ethyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethylcarbamate (203 mg, 0.50 mmol), <strong>[65938-77-4]5-methylpyridine-2-sulfonamide</strong> (86 mg, 0.50 mmol) and DBU (82 muL, 0.55 mmol) in acetonitrile (5 mL) was stirred for overnight at ambient temperature. Then, the volatile components were removed by evaporation and the residue was dissolved in dichloromethane. The organic phase was washed with water, dried (MgSO4) and concentrated. The residue was purified by TLC with dichloromethane/methanol (10:1) to afford 145 mg (60%) of the title compound as white solids: MS (ESI) m/z 490 [M+H]+, 488 [M-H]-, 1H-NMR (DMSO-d6) delta1.18 (3H, t, J=7.5 Hz), 2.37 (3H, s), 2.72-2.90 (4H, m), 3.23 (2H, q, J=6.0 Hz), 6.69 (1H, br), 7.40-7.59 (6H, m), 7.85-7.93 (4H, m), 8.24 (1H, s), 8.55 (1H, s).

References: [1]Patent: US2003/220372,2003,A1 .Location in patent: Page/Page column 35.

23
[ 1336-21-6 ]
[ 96042-30-7 ]
[ 18368-58-6 ]
[ 65938-77-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hypochlorite; In tetrahydrofuran;	b) To a mixture of 100 ml of 25% aqueous hydrochloric acid and 250 ml of DCM was added 18 g of 5-methyl-2-thio-pyridine. While the mixture was vigorously stirred and kept at -1 0 C. 250 ml of an aqueous solution containing 13% of sodium hypochlorite was carefully added. Upon completion of the addition, stirring was continued for 10 min. The organic layer was separated. To the aqueous layer 250 ml of DCM was added and the mixture was again treated as before with a further 250 ml batch of bleach. Upon completion of the addition, the organic layer was separated. The aqueous layer was extracted five times with 200 ml DCM. The organic layers were combined, dried over MgSO4 and evaporated. The resulting oil was dissolved in 125 ml of THF and cooled to -20 C. 25 ml of saturated aqueous ammonium hydroxide solution was slowly added. The mixture was stirred over night at room temperature. Excess of ammonia was neutralised by adding hydrochloric acid and the THF was removed in vacuo. The remaining aqueous solution was extracted three times with 150 ml of ethyl acetate. The combined organic layers were dried over MgSO4 and the solvent was evaporated. The remaining solid was recrystallized from boiling ethyl acetate to yield 13.35 g of 5-methyl-2-pyridine sulfonamide in form of beige crystals. 1H-NMR(D6-DMSO, 300 MHz): 2.37(s, 3H); 7.36(s, 2H); 7.78-7.85(m, 2H); 8.53(s, 1H); LC-MS: tR=2.32 min, [M+1]+=173.04, [M-1]-=171.10.

References: [1]Patent: US2003/87920,2003,A1 .

24
1,4-diazobicyclo-[2,2,2]-octane [ No CAS ]
[ 65938-77-4 ]
[ 285135-68-4 ]
[ 257876-24-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; potassium carbonate; In methanol; water; acetone;	EXAMPLE 3 12.5 g (33.5 mmol) of 4-[4,6-dichloro-5-(2-methoxy-phenoxy)-pyrimidine-2-yl]-pyridine-2-carbonitrile and 6.06 g (35 mmol) of <strong>[65938-77-4]5-methyl-pyridine-2-sulfonamide</strong> were added to 130 ml of acetone. 15 g of potassium carbonate and 190 mg (1.6 mmol) of 1,4-diazobicyclo[2.2.2]octane were added and the suspension was stirred at 40 C. for 5 hr and at 20 C. for 15 hr. Then 50 ml of de-ionized water were added followed by dropwise addition of 50 ml of 3 N hydrochloric acid (pH of the solution=1). Acetone was removed by evaporation and the suspension was stirred for 1 hr. The solid was filtered and washed with 100 ml of water. The residue was heated (reflux) in 100 ml of methanol for 1 hr followed by cooling to 20 C. The solid was filtered and dried at 80 C., 2000 Pa for 16 hr. There were obtained 16.0 g (93% of theory) of 5-methyl-pyridine-2-sulfonic acid [6-chloro-2-(2-cyano-pyridine-4-yl)-5-(2-methoxy-phenoxy)-pyrimidine-4-yl]-amide with a HPLC purity of 90.3% (w/w).

References: [1]Patent: US6103902,2000,A .

25
[ 3510-66-5 ]
[ 13598-45-3 ]
[ 110-18-9 ]
[ 7446-09-5 ]
[ 65938-77-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; sec.-butyllithium; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; cyclohexane; water;	PREPARATION 4 5-Methyl-2-pyridinesulfonamide STR142 Sec-butyllithium (9.8 ml of 1.3 M in cyclohexane) and N,N,N'N'-tetramethylethylenediamine (1.8 ml, 12.2 mmol) were added to a stirred solution of 2-bromo-5-methylpyridine (2 g, 11.6 mmol) at -78 C. under a nitrogen atmosphere. After 90 min sulphur dioxide (approximately 30 ml) was condensed into the reaction mixture using a cold finger and the reaction mixture was slowly warmed to room temperature over 12 h. The reaction mixture was concentrated to dryness and the residue dissolved in ice-water. To this was added a mixture of sodium hydroxide (1.39 g, 35 mmol) and hydroxylamine sulphonic acid (3.9 g, 35 mmol) in water (20 ml). After 24 h the solution was extracted with ethyl acetate, dried (MgSO4) and concentrated. Flash column chromatography (95% dichloromethane/5% methanol) gave the product (250 mg) as a clear oil which crystallized on standing. 1 H NMR (400 MHz, CDCl3): delta=2.40 (s, 3 H), 5.20 (brs, 2 H), 7.80 (d, 1 H), 7.90 (d, 1 H), 8.50 (s, 1 H). LRMS (Thermospray): 172.8 (MH+).

References: [1]Patent: US6017945,2000,A .

26
[ 592-41-6 ]
[ 65938-77-4 ]
[ 1019201-56-9 ]

References: [1]Organic Letters,2008,vol. 10,p. 1497 - 1500.

27
[ 3240-34-4 ]
[ 65938-77-4 ]
[ 1140917-86-7 ]

References: [1]Advanced Synthesis and Catalysis,2008,vol. 350,p. 1835 - 1840.

28
[ 65938-77-4 ]
[ 100-51-6 ]
[ 1118689-58-9 ]

References: [1]Tetrahedron Letters,2010,vol. 51,p. 2048 - 2051.
[2]Chemistry - A European Journal,2011,vol. 17,p. 1021 - 1028.
[3]Journal of the American Chemical Society,2009,vol. 131,p. 1775 - 1779.

29
[ 221674-85-7 ]
[ 65938-77-4 ]
[ 1201940-83-1 ]

References: [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 8452 - 8456.

30
[ 4382-54-1 ]
[ 65938-77-4 ]
[ 1201940-72-8 ]

References: [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 8452 - 8456.

31
8-cyclohexyl-11-methoxy-1a-((3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl)carbonyl)-1,1a,2,12b-tetrahydrocyclopropa[d]indolo[2,1-a][2]benzazepine-5-carboxylic acid trifluoroacetate [ No CAS ]
[ 65938-77-4 ]
8-cyclohexyl-11-methoxy-1a-((3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl)carbonyl)-N-((5-methyl-2-pyridinyl)sulfonyl)-1,1a,2,12b-tetrahydrocyclopropa[d]indolo[2,1-a][2]benzazepine-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		8-Cyclohexyl-11-methoxy-1a-((3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl)carbonyl)-1,1a,2,12b-tetrahydrocyclopropa[d]indolo[2,1-a][2]benzazepine-5-carboxylic acid TFA (400 mg, 0.61 mmol) was dissolved into THF (4 mL) and stirred under nitrogen. CDI (160 mg, 0.98 mmol) was added and the reaction mixture was heated at 60 C. for 2 h. The reaction was cooled to rt and then (0.50 mL) of the reaction solution was added to a stirring solution of <strong>[65938-77-4]5-methylpyridine-2-sulfonamide</strong> (30 mg, 0.17 mmol) in DBU (100 muL, 0.66 mmol) and THF (0.100 mL). The reaction was stirred 3 h (complete by LCMS), quenched with 1M HCl (ac) (0.75 mL) (slight exotherm was noted) and concentrated under a stream of nitrogen over 2d. The residue was dissolved into MeOH (1 mL) and purified in one injection by preparative HPLC (CH3CN/H2O with 10 mM NH4OAc) to yield 8-cyclohexyl-11-methoxy-1a-((3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl)carbonyl)-N-((5-methyl-2-pyridinyl)sulfonyl)-1,1a,2,12b-tetrahydrocyclopropa[d]indolo[2,1-a][2]benzazepine-5-carboxamide (35.9 mg, 0.051 mmol, 68% yield) as a yellow solid. The compound was isolated as a mixture of enantiomers and presents as a 1:2 mixture of rotamers or atrope isomers. 1H NMR (300 MHz, CDCl3) delta ppm 0.19-0.27 (m, 0.33H), 0.95-3.11 (m, 24.67H), 2.45 (s, 3H), 3.59 (d, J=14.6 Hz, 1H), 3.90 (s, 2H), 3.91 (s, 1H), 4.02 (d, J=14.6 Hz, 0.33H), 4.15 (d, J=14.6 Hz, 0.33H), 4.64-4.26 (m, 1.67H), 5.12 (d, J=14.6 Hz, 0.67H), 6.95-7.03 (m, 1H) 7.15 (d, J=2.6 Hz, 0.33H), 7.19 (d, J=2.6 Hz, 0.67H), 7.30 (d, J=8.4 Hz, 0.67H), 7.31 (d, J=8.8 Hz, 0.33H), 7.66-7.84 (m, 3H), 8.03-8.10 (m, 1.67H), 8.22 (s, 0.33H), 8.44 (s, 1H). LC-MS retention time: 2.19 min; m/z 706 (MH-). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 10 u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 4 min, a hold time of 1 min, and an analysis time of 5 min where solvent A was 5% acetonitrile/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% acetonitrile/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

References: [1]Patent: US2009/130057,2009,A1 .Location in patent: Page/Page column 51.

32
[ 65938-77-4 ]
[ 1148-11-4 ]
[ 1254106-80-3 ]

References: [1]Journal of Organic Chemistry,2010,vol. 75,p. 7279 - 7290.

33
[ 65938-77-4 ]
[ 99685-96-8 ]
[ 1414835-98-5 ]

References: [1]Chemistry - A European Journal,2012,vol. 18,p. 12035 - 12045.

34
[ 65938-77-4 ]
C₂₅H₂₈N₂O₅S [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 1848 - 1853.

35
[ 65938-77-4 ]
[ 3355-28-0 ]
N,N-bis(2-butynyl)-(5-methyl-2-pyridyl)sulfonamide [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 1848 - 1853.

Historical Records

Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 65938-77-4 ]

Amines

A168147 [63636-89-5]

Pyridine-2-sulfonamide

Similarity: 0.92

A604749 [65938-79-6]

3-Methylpyridine-2-sulfonamide

Similarity: 0.87

A322579 [75903-58-1]

6-Aminopyridine-2-sulfonamide

Similarity: 0.84

A400319 [856013-04-2]

6-Bromopyridine-2-sulfonamide

Similarity: 0.77

A194461 [314250-03-8]

N,N-Diethylpyridine-2-sulfonamide

Similarity: 0.73

Sulfamides

A168147 [63636-89-5]

Pyridine-2-sulfonamide

Similarity: 0.92

A604749 [65938-79-6]

3-Methylpyridine-2-sulfonamide

Similarity: 0.87

A322579 [75903-58-1]

6-Aminopyridine-2-sulfonamide

Similarity: 0.84

A400319 [856013-04-2]

6-Bromopyridine-2-sulfonamide

Similarity: 0.77

A194461 [314250-03-8]

N,N-Diethylpyridine-2-sulfonamide

Similarity: 0.73

Related Parent Nucleus of
[ 65938-77-4 ]

Pyridines

A168147 [63636-89-5]

Pyridine-2-sulfonamide

Similarity: 0.92

A604749 [65938-79-6]

3-Methylpyridine-2-sulfonamide

Similarity: 0.87

A322579 [75903-58-1]

6-Aminopyridine-2-sulfonamide

Similarity: 0.84

A400319 [856013-04-2]

6-Bromopyridine-2-sulfonamide

Similarity: 0.77

A194461 [314250-03-8]

N,N-Diethylpyridine-2-sulfonamide

Similarity: 0.73

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CAS No.: 65938-77-4

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