1,2-Dichloroethane → HCID 178495642, compound

HRID 1258753Notes

Reaction equation

HRID 1258753 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N:9]2[CH2:13][CH2:12][CH2:11][C@H:10]2[CH2:14][O:15][CH3:16])=[CH:4][C:3]=1[NH:17][C:18](=S)[NH:19][C:20]1[CH:21]=[C:22]([CH:34]=[CH:35][C:36]=1[Cl:37])[CH2:23][NH:24][C:25]([C:27]1([C:30]([F:33])([F:32])[F:31])[CH2:29][CH2:28]1)=[O:26].C(Cl)CCl.CN(C=O)C>[Cl-].[Na+].O>[Cl:37][C:36]1[CH:35]=[CH:34][C:22]([CH2:23][NH:24][C:25]([C:27]2([C:30]([F:33])([F:32])[F:31])[CH2:29][CH2:28]2)=[O:26])=[CH:21][C:20]=1[NH:19][C:18]1[NH:17][C:3]2[CH:4]=[C:5]([N:9]3[CH2:13][CH2:12][CH2:11][C@H:10]3[CH2:14][O:15][CH3:16])[C:6]([Cl:8])=[CH:7][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 86674358(S)-N-(3-(3-(2-Amino-4-chloro-5-(2-(methoxymethyl)pyrrolidin-1-yl)phenyl)thioureido)-4-chlorobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

Product 1

HCID 178495642HCID 178495642, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (S)—N-(3-(3-(2-amino-4-chloro-5-(2-(methoxymethyl)pyrrolidin-1-yl)phenyl)thioureido)-4-chlorobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide (110 mg; 0.19 mmol), EDC (36 mg; 0.19 mmol) and DMF (4 mL) was stirred at 90° C. overnight. The mixture was poured into brine and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated and the residue was purified by column chromatography.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-22de824c786a4525be28856cb845512c
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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