Cyclopentanecarbonyl chloride → HCID 59631243, compound

HRID 1431678Notes

Reaction equation

HRID 1431678 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:26]=1)=[C:5]([CH3:19])[C:6]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[N:7]2.[CH:33]1([C:38](Cl)=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34]1>>[CH:33]1([C:38]([N:16]2[CH2:15][CH2:14][N:13]([C:6]3[C:5]([CH3:19])=[C:4]([NH:20][C:21]4[CH:22]=[N:23][CH:24]=[C:25]([N:27]5[CH2:32][CH2:31][O:30][CH2:29][CH2:28]5)[CH:26]=4)[C:3]4[C:8](=[CH:9][C:10]([F:12])=[CH:11][C:2]=4[F:1])[N:7]=3)[CH2:18][CH2:17]2)=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

3

Reactant 2

HCID 78284Cyclopentanecarbonyl chlorideHCID 596310285,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine

Product 1

HCID 59631243HCID 59631243, compound

Procedure

Prepared according to Procedure R using 5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine (40.0 mg, 0.09 mmol) and cyclopentanecarbonyl chloride to give cyclopentyl(4-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)piperazin-1-yl)methanone. 1H NMR (DMSO-d6) δ ppm 1.51-1.73 (m, 8H), 2.10 (br s, 3H), 3.00 (m, 1H), 3.00-3.07 (m, 4H), 3.24 (br s, 2H), 3.33 (br s, 4H), 3.65-3.70 (m, 6H), 6.51 (br s, 1H), 7.13-7.19 (m, 1H), 7.27-7.30 (m, 1H), 7.52 (d, J=2.0 Hz, 1H), 7.78 (d, J=2.4 Hz, 1H), 8.37 (s, 1H). Mass Spectrum (ESI) m/e=537.4 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-de0363949ffd4e0d98cd687bb569715c
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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