1-(3-Aminopropyl)-2-pyrrolidinone → 8-(2,6-Difluorophenyl)-4-(4-fluoro-2-methylphenyl)-2-[[3-(2-oxo-1-pyrrolidinyl)propyl]amino]pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 2357323Notes

Reaction equation

HRID 2357323 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].[NH2:32][CH2:33][CH2:34][CH2:35][N:36]1[CH2:40][CH2:39][CH2:38][C:37]1=[O:41]>>[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:32][CH2:33][CH2:34][CH2:35][N:36]3[CH2:40][CH2:39][CH2:38][C:37]3=[O:41])[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

3

Reactant 2

HCID 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 596395548-(2,6-difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 445361208-(2,6-Difluorophenyl)-4-(4-fluoro-2-methylphenyl)-2-[[3-(2-oxo-1-pyrrolidinyl)propyl]amino]pyrido[2,3-d]pyrimidin-7(8H)-oneYield 85.1%

Procedure

Following the general procedure outlined in Example 225, the product of Example 48 (100 mg, 0.22 mmol) and N-(3′-aminopropyl)-2-pyrrolidinone (96 mg, 0.67 mmol) were reacted to give the crude material. Purification by flash chromatography eluting with EtOAc/hexane/triethylamine (70/30/2, v/v/v), followed by recrystallization from ethanol and hexane, gave the desired product 95 mg (85%). LC-MS: 508.2 (MH+, m/z), 2.02 (Rt, min).

Workup

  1. customto give the crude material
  2. customPurification by flash chromatography
  3. washeluting with EtOAc/hexane/triethylamine (70/30/2, v/v/v)
  4. customfollowed by recrystallization from ethanol and hexane

Sources & evidence

ORD record
ord-a7a6e71c994743c5beab0dc992cd3903
Source dataset
uspto-grants-2010_07
Patent number
US07759486B2

Reaction notes

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