Ethyl chloroformate → Ethyl 4-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)piperazine-1-carboxylate

HRID 1431669Notes

Reaction equation

HRID 1431669 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.Cl[C:34]([O:36][CH2:37][CH3:38])=[O:35]>>[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[CH2:14][CH2:15][N:16]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:17][CH2:18]1)=[N:7]2

Participants

3

Reactant 2

HCID 10928Ethyl chloroformateHCID 596310285,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine

Product 1

HCID 57449785Ethyl 4-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)piperazine-1-carboxylate

Procedure

Prepared according to Procedure N using 5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine (50 mg, 0.11 mmol) and ethyl chloroformate to give ethyl 4-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)piperazine-1-carboxylate. 1H NMR (DMSO-d6) δ ppm 1.09 (t, J=7.2 Hz, 3H), 2.13 (s, 3H), 3.04-3.06 (m, 4H), 3.27 (s, 4H), 3.55 (s, 4H), 3.68-3.70 (m, 4H), 4.08 (q, J=6.8 Hz, 2H,), 6.49 (m, 1H), 7.14-7.20 (m, 1H), 7.29 (dd, J=9.8 Hz, J=2 Hz, 1H), 7.52 (d, J=1.6 Hz, 1H), 7.78 (d, J=2 Hz, 1H), 8.38 (s, 1H). Mass Spectrum (ESI) m/e=513.1 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-c010ed2ee53e44d0add39cd6b082fa7c
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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