Methyl chloroformate → HCID 59631306, compound

HRID 1431665Notes

Reaction equation

HRID 1431665 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.Cl[C:35]([O:37][CH3:38])=[O:36]>>[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:35]([O:37][CH3:38])=[O:36])[C@@H:15]([CH3:19])[CH2:14]1)=[N:7]2

Participants

3

Reactant 2

HCID 6586Methyl chloroformateHCID 59631072HCID 59631072, compound

Product 1

HCID 59631306HCID 59631306, compound

Procedure

Essentially 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 mg, 0.11 mmol) and methyl chloroformate to give (S)-methyl 4-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)-2-methylpiperazine-1-carboxylate. 1H NMR (CDCl3) δ ppm 7.94 (1H, d, J=2.3 Hz), 7.69 (1H, d, J=2.2 Hz), 7.30 (1H, ddd, J=10.0, 2.6, 1.3 Hz), 6.89 (1H, d, J=12.9 Hz), 6.81 (1H, ddd, J=13.9, 8.8, 2.5 Hz), 6.58 (1H, t, J=2.4 Hz), 4.43 (1H, br. s.), 4.03 (1H, d, J=13.5 Hz), 3.86 (4H, dd, J=5.7, 3.9 Hz), 3.76 (3H, s), 3.71 (1H, d, J=9.8 Hz), 3.52-3.64 (1H, m), 3.38 (1H, td, J=12.8, 3.2 Hz), 3.17 (4H, dd, J=5.7, 4.1 Hz), 3.12 (1H, dd, J=12.8, 3.8 Hz), 2.93 (1H, td, J=12.6, 3.4 Hz), 2.10 (3H, s), 1.32 (3H, d, J=6.8 Hz). Mass Spectrum (ESI) m/e=513.3 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-346a0b6ab1674a30afb2880764fd6f86
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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