Methyl Isocyanate → HCID 67508737, compound

HRID 1431696Notes

Reaction equation

HRID 1431696 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:21][C:22]1[CH:23]=[N:24][CH:25]=[C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[CH:27]=1)=[C:5]([CH3:20])[C:6]([N:13]1[CH2:18][CH2:17][NH:16][C@@H:15]([CH3:19])[CH2:14]1)=[N:7]2.[CH3:34][N:35]=[C:36]=[O:37]>>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:21][C:22]1[CH:23]=[N:24][CH:25]=[C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[CH:27]=1)=[C:5]([CH3:20])[C:6]([N:13]1[CH2:18][CH2:17][N:16]([C:36]([NH:35][CH3:34])=[O:37])[C@@H:15]([CH3:19])[CH2:14]1)=[N:7]2

Participants

3

Reactant 2

HCID 12228Methyl IsocyanateHCID 59631072HCID 59631072, compound

Product 1

HCID 67508737HCID 67508737, compound

Procedure

Prepared according to Procedure N using (S)-5,7-difluoro-3-methyl-2-(3-methylpiperazin-1-yl)-N-(5-morpholinopyridin-3-yl)quinolin-4-amine (50.0 mg, 0.11 mmol) and methylisocyanate to give (S)-4-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)-N,2-dimethylpiperazine-1-carboxamide. 1H NMR (CDCl3) δ ppm 7.94 (1H, d, J=2.5 Hz), 7.69 (1H, d, J=2.2 Hz), 7.30 (1H, ddd, J=10.0, 2.5, 1.2 Hz), 6.90 (1H, d, J=13.3 Hz), 6.81 (1H, ddd, J=13.8, 8.7, 2.5 Hz), 6.59 (1H, t, J=2.3 Hz), 4.49 (1H, q, J=4.9 Hz), 4.18-4.31 (1H, m), 3.78-3.91 (5H, m), 3.69-3.78 (1H, m), 3.60 (1H, dt, J=12.8, 1.7 Hz), 3.37 (1H, td, J=12.4, 3.1 Hz), 3.09-3.23 (5H, m), 2.96 (1H, td, J=12.4, 3.5 Hz), 2.87 (3H, d, J=4.7 Hz), 2.10 (3H, s), 1.31 (3H, d). Mass Spectrum (ESI) m/e=512.2 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-3cfa6168e152429dac4879e2922212a6
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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