1,1-Dimethylethyl 4-(4-amino-2-fluorophenyl)-1-piperazinecarboxylate → HCID 66760728, compound

HRID 1188726Notes

Reaction equation

HRID 1188726 reaction equation
[CH2:1]([N:3]1[C:8]2[N:9]=[C:10](S(C)=O)[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:4]1=[O:22])[CH3:2].[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][N:33]([C:36]2[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][C:37]=2[F:43])[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>>[CH2:1]([N:3]1[C:8]2[N:9]=[C:10]([NH:42][C:39]3[CH:40]=[CH:41][C:36]([N:33]4[CH2:34][CH2:35][N:30]([C:28]([O:27][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:29])[CH2:31][CH2:32]4)=[C:37]([F:43])[CH:38]=3)[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:4]1=[O:22])[CH3:2]

Participants

3

Reactant 2

HCID 162036301,1-Dimethylethyl 4-(4-amino-2-fluorophenyl)-1-piperazinecarboxylateHCID 667609868-Ethyl-2-(methylsulfinyl)-6-phenylpyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 66760728HCID 66760728, compoundYield 21.1%

Procedure

8-ethyl-2-(methylsulfinyl)-6-phenylpyrido[2,3-d]pyrimidin-7(8H)-one (120 mg, 0.38 mmol) and 4-(4-amino-2-fluorophenyl)piperazine-1-carboxylic acid tert-butyl ester (113 mg, 0.38 mmol) were stirred at 120° C. for 3 h. The reaction mixture was purified by silica gel column chromatography using hexane:ethyl acetate (3:2). The isolated product was recrystallized from isopropanol to give the title compound (45 mg, 0.08 mmol, 21%) as a pale yellow solid. ESMS m/z 545 (M+H)+.

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography
  2. customThe isolated product was recrystallized from isopropanol

Sources & evidence

ORD record
ord-e5455f346b2d42088cad99f6cad9c4dc
Source dataset
uspto-grants-2014_03
Patent number
US08674095B2

Reaction notes

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