N-methyl-2-pyrrolidone → HCID 178521288, compound

HRID 900730Notes

Reaction equation

HRID 900730 reaction equation
CS[C:3]1[NH:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12]N=C[CH:9]=2)[N:4]=1.[NH2:14][CH2:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1)=[O:17].[CH3:26][N:27]1C(=O)CCC1>>[Cl:25][C:21]1[CH:20]=[C:19]([NH:18][C:16](=[O:17])[CH2:15][NH:14][C:3]2[NH:7][N:6]=[C:5]([C:8]3[CH:9]=[N:27][CH:26]=[CH:12][CH:13]=3)[N:4]=2)[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 22690363HCID 22690363, compoundHCID 178503395HCID 178503395, compound

Product 1

HCID 178521288HCID 178521288, compoundYield 85%

Conditions

Temperature
140 °C

Procedure

The sulfone from Step B (101 mg, 0.567 mmol) was dissolved in NMP (2 ml). To this solution 2-amino-N-(3-chlorophenyl)-acetamide (116 mg, 5 mmol) was added, and the mixture was heated at 140° C. for 12 h. The mixture was loaded directly onto an HPLC reverse phase column and purified by water to acetonitrile gradient in the presence of 0.1% trifluoroacetic acid. The aqueous phase was evaporated by lyophilization to yield the title compound as a fluffy white solid (166 mg, 85% yield). ES (MS): 345.12 (M+H)+

Workup

  1. custompurified by water to acetonitrile gradient in the presence of 0.1% trifluoroacetic acid
  2. customThe aqueous phase was evaporated by lyophilization

Sources & evidence

ORD record
ord-760e0727b39e4eab8f7a7c5ddd5878a4
Source dataset
uspto-grants-2008_04
Patent number
US07361669B2

Reaction notes

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