Benzamide → HCID 178456215, compound

HRID 1014428Notes

Reaction equation

HRID 1014428 reaction equation
C(N)(=O)C1C=CC=CC=1.Cl[C:11]1[N:12]=[C:13]([NH:30][C:31]2[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[C:32]=2[C:33]([NH2:35])=[O:34])[C:14]2[CH:19]=[CH:18][N:17](S(C3C=CC(C)=CC=3)(=O)=O)[C:15]=2[N:16]=1.[OH-].[NH4+].[CH3:43][O:44][C:45]1[CH:51]=[C:50]([CH:52]2[CH2:57][CH2:56][N:55]([CH2:58][CH2:59][CH3:60])[CH2:54][CH2:53]2)[CH:49]=[CH:48][C:46]=1[NH2:47]>>[F:40][C:36]1[CH:37]=[CH:38][CH:39]=[C:31]([NH:30][C:13]2[N:12]=[C:11]([NH:47][C:46]3[CH:48]=[CH:49][C:50]([CH:52]4[CH2:53][CH2:54][N:55]([CH2:58][CH2:59][CH3:60])[CH2:56][CH2:57]4)=[CH:51][C:45]=3[O:44][CH3:43])[NH:16][C:15]3=[N:17][CH:18]=[CH:19][C:14]=23)[C:32]=1[C:33]([NH2:35])=[O:34]

Participants

5

Reactant 4

HCID 2331BenzamideHCID 14923Ammonium HydroxideHCID 598602732-Methoxy-4-(1-propylpiperidin-4-yl)anilineHCID 866441882-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzamide

Product 1

HCID 178456215HCID 178456215, compoundYield 34.8%

Procedure

According to General Protocol III, 2-fluoro-6-[(2-{[2-methyloxy)-4-(1-propyl-4-piperidinyl)phenyl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]benzamide was prepared from 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzamide (0.30 g, 0.65 mmol), 27% aqueous ammonium hydroxide, and 2-(methyloxy)-4-(1-propyl-4-piperidinyl)aniline (0.18 g, 0.72 mmol) and isolated as a yellow solid (0.117 g); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.85 (t, J=7.5 Hz, 3H), 1.45 (dq, J=14.9, 7.4 Hz, 2 H), 1.64-1.75 (m, 4 H), 1.88-1.98 (m, 2 H), 2.19-2.27 (m, 2 H), 2.42 (dt, J=7.4, 3.8 Hz, 1 H), 2.95 (d, J=11.0 Hz, 2 H), 3.84 (s, 3 H), 6.23 (dd, J=3.5, 2.0 Hz, 1 H), 6.76 (dd, J=8.4, 1.5 Hz, 1 H), 6.87 (d, J=1.5 Hz, 1 H), 6.90-7.00 (m, 2 H), 7.39-7.48 (m, 2 H), 8.01 (s, 1 H), 8.08 (s, 1 H), 8.17 (d, J=8.1 Hz, 1 H), 8.42 (d, J=8.4 Hz, 1 H), 10.42 (s, 1 H), 11.39 (s, 1 H); ESIMS (M+H)+=518.

Sources & evidence

ORD record
ord-72542f011f3f4a04972ed01b30a012e1
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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