N-methyl-2-pyrrolidone → HCID 178434062, compound

HRID 2249848Notes

Reaction equation

HRID 2249848 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](S(C)(=O)=O)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:31].[CH3:32][C:33]1[NH:34][C:35](NC)=[N:36][N:37]=1.[CH3:40][N:41]1C(=O)CCC1>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:41][CH2:40][C:35]3[NH:34][C:33]([CH3:32])=[N:37][N:36]=3)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:31]

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 596395548-(2,6-difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-oneHCID 178482496HCID 178482496, compound

Product 1

HCID 178434062HCID 178434062, compoundYield 14%

Procedure

A solution of the product of Example 48 (150 mg, 0.34 mmol) and (5-methyl-4H-[1,2,4]triazol-3-yl)-methylamine (190 mg, 1.7 mmol) in NMP (2 mL) was stirred at 100° for 16 h to give the crude material. Preparative HPLC, eluting with acetonitrile/H2O (10/90, v/v to 90/10, v/v, over 10 min), gave the desired product 23 mg (14%). LC-MS: 478.2 (MH+, m/z), 1.70 (Rt, min).

Workup

  1. customto give the crude material
  2. washPreparative HPLC, eluting with acetonitrile/H2O (10/90, v/v to 90/10

Sources & evidence

ORD record
ord-454d242c9b1b4a96a86bb33dba224b6d
Source dataset
uspto-grants-2008_01
Patent number
US07314881B2

Reaction notes

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