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Chemical Structure| 39987-25-2 Chemical Structure| 39987-25-2
Chemical Structure| 39987-25-2

Dimethyl 2,2'-azanediyldiacetate hydrochloride

CAS No.: 39987-25-2

4.5 *For Research Use Only !

Cat. No.: A147944 Purity: 98%

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Product Details of [ 39987-25-2 ]

CAS No. :39987-25-2
Formula : C6H12ClNO4
M.W : 197.62
SMILES Code : O=C(OC)CNCC(OC)=O.[H]Cl
MDL No. :MFCD00216724
InChI Key :IIWYYIACSUPJCN-UHFFFAOYSA-N
Pubchem ID :2727727

Safety of [ 39987-25-2 ]

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

Calculated chemistry of [ 39987-25-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 0
Fraction Csp3 0.67
Num. rotatable bonds 6
Num. H-bond acceptors 5.0
Num. H-bond donors 1.0
Molar Refractivity 43.29
TPSA ?

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

64.63 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

0.44
Log Po/w (WLOGP)?

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

-0.28
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.

-0.23
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

-0.3
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.07

Water Solubility

Log S (ESOL):?

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

-0.95
Solubility 22.4 mg/ml ; 0.113 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.

-1.37
Solubility 8.53 mg/ml ; 0.0432 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

-0.88
Solubility 25.8 mg/ml ; 0.131 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.

-7.19 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

1.0 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)

1.54

Application In Synthesis of [ 39987-25-2 ]

* 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 [ 39987-25-2 ]

[ 39987-25-2 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 67-56-1 ]
  • [ 628-87-5 ]
  • [ 39987-25-2 ]
  • 2
  • [ 123-75-1 ]
  • [ 39987-25-2 ]
  • [ 111605-86-8 ]
  • 3
  • [ 4857-04-9 ]
  • [ 39987-25-2 ]
  • [ 89218-91-7 ]
  • 4
  • [ 4760-35-4 ]
  • [ 39987-25-2 ]
  • [ 89218-98-4 ]
  • 5
  • [ 72998-92-6 ]
  • [ 39987-25-2 ]
  • [Carboxymethyl-(5,6-dimethyl-1H-benzoimidazol-2-ylmethyl)-amino]-acetic acid [ No CAS ]
  • 6
  • [ 39811-03-5 ]
  • [ 39987-25-2 ]
  • [Carboxymethyl-(5,6-dichloro-1H-benzoimidazol-2-ylmethyl)-amino]-acetic acid [ No CAS ]
  • 7
  • [ 14625-39-9 ]
  • [ 39987-25-2 ]
  • [Carboxymethyl-(5-nitro-1H-benzoimidazol-2-ylmethyl)-amino]-acetic acid [ No CAS ]
  • 8
  • [ 7192-00-9 ]
  • [ 39987-25-2 ]
  • [(1-Benzyl-1H-benzoimidazol-2-ylmethyl)-carboxymethyl-amino]-acetic acid [ No CAS ]
  • 9
  • [ 13122-90-2 ]
  • [ 39987-25-2 ]
  • [ 143674-08-2 ]
  • 10
  • [ 39987-25-2 ]
  • 2-Chloromethyl-1-phenethyl-1H-benzoimidazole [ No CAS ]
  • [Carboxymethyl-(1-phenethyl-1H-benzoimidazol-2-ylmethyl)-amino]-acetic acid [ No CAS ]
  • 11
  • [ 39987-25-2 ]
  • [ 89218-88-2 ]
  • [Carboxymethyl-(5-iodo-1H-benzoimidazol-2-ylmethyl)-amino]-acetic acid [ No CAS ]
  • 12
  • [ 39987-25-2 ]
  • [ 80567-68-6 ]
  • [Carboxymethyl-(5-methyl-1H-benzoimidazol-2-ylmethyl)-amino]-acetic acid [ No CAS ]
  • 13
  • [ 39987-25-2 ]
  • [ 1740-88-1 ]
  • [(5-Bromo-1H-benzoimidazol-2-ylmethyl)-carboxymethyl-amino]-acetic acid [ No CAS ]
  • 14
  • [ 39987-25-2 ]
  • [ 20443-38-3 ]
  • [Carboxymethyl-(5-chloro-1H-benzoimidazol-2-ylmethyl)-amino]-acetic acid [ No CAS ]
  • 15
  • [ 39987-25-2 ]
  • [ 79-04-9 ]
  • [ 106817-57-6 ]
  • 16
  • [ 39987-25-2 ]
  • 5-Butyl-2-chloromethyl-1H-benzoimidazole [ No CAS ]
  • [(5-Butyl-1H-benzoimidazol-2-ylmethyl)-carboxymethyl-amino]-acetic acid [ No CAS ]
  • 17
  • [ 39987-25-2 ]
  • [ 108-24-7 ]
  • [ 5410-10-6 ]
YieldReaction ConditionsOperation in experiment
82% With triethylamine; at 0 - 20℃; for 4.5h; Acetic anhydride (9.1 ml, 96.7 mmol) was added dropwise at 0Cinto a solution <strong>[39987-25-2]dimethyl 2,2'-azanediyldiacetate hydrochloride</strong>4(14.70 g, 74.39 mmol) in triethylamine (50 ml). The reaction mixture was stirred for 0.5 h and then transferred to room temperature and stirred for 4 h. Triethylamine was removed under vacuum. The residue was extracted with dichloromethane and the organic phase was washed with saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by recrystallization from dichloromethane / n-hexane to give the compound5(12.39 g, 82%yield) as a white solid.1H NMR (500 MHz, CDCl3) delta 4.20 (s, 2H), 4.15 (s, 2H), 3.78 (s, 3H), 3.72 (s,3H), 2.12 (s, 3H). HRMS (ESI) (m/z):calcdfor C8H13NO5[M+H]+ 204.0872, found. 204.0864. [M+Na]+ 226.0691, found.226.0681.
82% With triethylamine; at 0 - 20℃; for 4.5h; Compound 2 (14.70 g, 74.39 mmol) was dissolved in 50 ml of triethylamine. The reaction solution was placed in an ice bath at 0 C, and acetic anhydride (9.1 ml, 96.7 mmol) was added. After 0.5 h of reaction, it was transferred to room temperature and stirred at room temperature for 4 h. Remove the solvent by spin. The reaction solution was extracted with dichloromethane / water. The dichloromethane phase was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated by rotary evaporation. The crude product was recrystallized from dichloromethane / n-hexane to give Compound 3 (12.39 g, 82%) as a white solid.
  • 18
  • [ 10563-26-5 ]
  • [ 39987-25-2 ]
  • 1,4,7,11,14-Pentaaza-cycloheptadecane-2,6-dione; hydrochloride [ No CAS ]
  • 19
  • [ 39987-25-2 ]
  • [ 112-24-3 ]
  • 2,6-dioxo-1,4,7,10,13-pentaazacyclopentadecane [ No CAS ]
  • 20
  • [ 39987-25-2 ]
  • [ 200730-91-2 ]
  • [ 226985-09-7 ]
  • 21
  • [ 39987-25-2 ]
  • [ 81998-05-2 ]
  • [ 344367-58-4 ]
  • 22
  • [ 683-57-8 ]
  • [ 39987-25-2 ]
  • (4-methyloxycarbonylmethyl)piperazine-2,6-dione [ No CAS ]
  • 23
  • [ 67-56-1 ]
  • [ 142-73-4 ]
  • [ 39987-25-2 ]
YieldReaction ConditionsOperation in experiment
99% With thionyl chloride; at -10 - 20℃; Thionyl chloride (16 ml, 225.39 mmol, 1.64 g/ml) the addition was completed, iminodiacetic acid3(10 g, 75.13 mmol) was added and the reaction was transferred to room temperature,stiringovernight. Methanol was removed under vacuum to give the compound4(14.70 g, 99 %) as a white solid.1H NMR (400 MHz, DMSO) delta10.05 (s, 2H), 4.01 (s, 4H), 3.74 (s, 6H). HRMS (ESI) (m/z):calcdfor C6H11NO4[M+H]+ 162.0755, found. 162.0766.
99% With thionyl chloride; at -10 - 20℃; At -10 , pressure-equalizing dropping funnel was added thionyl chloride (16ml, 225.39mmol, 1.64g / ml)To 100 ml of methanol, add imine diacetate (10 g, 75.13 mmol),The reaction solution was transferred to room temperature and stirred overnight. The reaction solution was swirled to remove methanol to obtain Compound 3 (14.70 g, 99%) as a white solid.
81% Methanol (500 mL) was cooled to -20 C, and SOCl2 (36 mL, 0.5 mol) was added dropwise under vigorous stirring while maintaining the temperature of the reaction mixture below -10 C. Iminodiacetic acid(13.3 g, 0.1 mol) was then added in one portion. The reaction mixture was stirred for 24 h at r.t. and then left to stand at r.t. for two days.The volatiles were evaporated, and the residue were crystallized from methanol. Yield: 16 g (81%); white crystalline solid.1H NMR (300 MHz, D2O): delta = 4.13 (s, 4 H), 3.85 (s, 6 H).13C NMR (75 MHz, D2O): delta = 168.08, 54.12, 47.66. Anal. Calcd for C6H12ClNO4: C, 36.47; H, 6.12; N, 7.09. Found: C, 36.52;H, 6.01; N, 6.98.
  • 24
  • [ 16004-15-2 ]
  • [ 39987-25-2 ]
  • [ 6096-66-8 ]
  • 25
  • [ 111-19-3 ]
  • [ 39987-25-2 ]
  • cis-2,5-bis(methoxycarbonyl)-pyrrolidino[60]fullerene [ No CAS ]
  • C82H34N2O10 [ No CAS ]
  • 26
  • [ 39987-25-2 ]
  • [ 99685-96-8 ]
  • [ 121-44-8 ]
  • 1'-methoxycarbonylmethyl-2'-methylpyrrolidino[3',4':1,9](C60-Ih)[5,6]fullerene [ No CAS ]
  • 27
  • [ 39987-25-2 ]
  • 2-benzyloxycarbonylamino-3-{4-[(bis-methoxycarbonylmethyl-amino)-methyl]-phenyl}-propionic acid <i>tert</i>-butyl ester [ No CAS ]
  • 28
  • [ 39987-25-2 ]
  • (2S,3R,5S)-5-Acetylamino-3-hydroxy-1-methoxycarbonylmethyl-6-oxo-3-phenyl-piperidine-2-carboxylic acid methyl ester [ No CAS ]
  • 29
  • [ 39987-25-2 ]
  • [ 106817-60-1 ]
  • 30
  • C8H8BrO2Pol [ No CAS ]
  • [ 39987-25-2 ]
  • C14H18NO6Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 24h; An other tridentate ligand, yielding negatively charged complexes, was attached to the same resin as in example 1. Dimethylimino diacetate hydrochloride (6.4 mg, 33 [FMOL)] and diisopropylethylamine (11.2 [PL,] 66 [PMOL)] were dissolved in DMF (0.5 ml) and resin 1 (280 mg, 67 [FMOL)] was added. The mixture was gently stirred at room temperature for 24 hours, the reaction mixture was filtered, and the resin was washed with DMF (3 times), DMF and methanol (3 times alternating), methanol and water (3 times alternating). The protected intermediate was positive on bromophenol blue and negative on TNBS staining. The protecting groups were removed rinsing the resin with aqueous NaOH (0. [1M] for 3 hours, then 0.01M for 12 hours). Filtration of the resin, washing with [NAOH] [0.] 1M (2 times), water (5 times), water and methanol (3 times alternating), methanol (3 times), and diethyl ether (3 times) and drying at high vacuum gave product 5 in an yield of 35 mg (100%; capacity 4 mmol/g, coupling efficiency 18%). Resin 5 was negative on all of the staining reactions.
 

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