3,5-Dichloro-4-(2-(dimethylamino)acetamido)-benzylamine → HCID 178483944, compound

HRID 2217768Notes

Reaction equation

HRID 2217768 reaction equation
CS[C:3](=[N:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[NH:4][C:5]([C@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)=[O:6].[Cl:30][C:31]1[CH:32]=[C:33]([CH:36]=[C:37]([Cl:46])[C:38]=1[NH:39][C:40](=[O:45])[CH2:41][N:42]([CH3:44])[CH3:43])[CH2:34][NH2:35]>C(N(CC)CC)C>[Cl:30][C:31]1[CH:32]=[C:33]([CH:36]=[C:37]([Cl:46])[C:38]=1[NH:39][C:40](=[O:45])[CH2:41][N:42]([CH3:43])[CH3:44])[CH2:34][NH:35][C:3]([NH:4][C:5]([C@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)=[O:6])=[N:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 589629233,5-Dichloro-4-(2-(dimethylamino)acetamido)-benzylamineHCID 58986296(R)-tert-butyl methylthio(1-(4-(trifluoromethyl)-phenyl)pyrrolidine-2-carboxamido)methylenecarbamate

Product 1

HCID 178483944HCID 178483944, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of (R)-tert-butyl methylthio(1-(4-(trifluoromethyl)-phenyl)pyrrolidine-2-carboxamido)methylenecarbamate (6 mg), 3,5-dichloro-4-(2-(dimethylamino)acetamido)-benzylamine (10 mg) and triethylamine (50 μL) was heated at 56° C. for 12 h. The crude reaction mixture was purified directly by preparative TLC eluting with 10% methanol/89% dichloromethane/1% ammonia hydroxide to give the title compound as a colorless oil (5 mg). retention time: 2.03 min (method A). MS (ESI) (M+Na)+ 659.19.

Workup

  1. customThe crude reaction mixture
  2. customwas purified directly by preparative TLC
  3. washeluting with 10% methanol/89% dichloromethane/1% ammonia hydroxide

Sources & evidence

ORD record
ord-3f446c5f047a46d7ab0f52e13dba81e0
Source dataset
uspto-grants-2008_08
Patent number
US07408071B2

Reaction notes

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