Ammonium Hydroxide → HCID 178456224, compound

HRID 1014441Notes

Reaction equation

HRID 1014441 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:23]=2[C:24]([NH2:26])=[O:25])[C:5]2[CH:10]=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:6]=2[N:7]=1.[OH-].[NH4+].[CH3:35][O:36][C:37]1[CH:43]=[C:42]([C:44]2[CH2:45][N:46]([CH2:50][CH2:51][CH3:52])[CH2:47][CH2:48][CH:49]=2)[CH:41]=[CH:40][C:38]=1[NH2:39]>>[F:31][C:29]1[C:28]([F:32])=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[C:22]([NH:21][C:4]2[N:3]=[C:2]([NH:39][C:38]3[CH:40]=[CH:41][C:42]([C:44]4[CH2:45][N:46]([CH2:50][CH2:51][CH3:52])[CH2:47][CH2:48][CH:49]=4)=[CH:43][C:37]=3[O:36][CH3:35])[NH:7][C:6]3=[N:8][CH:9]=[CH:10][C:5]=23)[CH:30]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 59441706HCID 59441706, compoundHCID 86644191HCID 86644191, compound

Product 1

HCID 178456224HCID 178456224, compoundYield 12%

Procedure

According to General Protocol III, 4,5-difluoro-2-[4(2-{[2-(methyloxy)-4-(1-propyl-1,2,5,6-tetrahydro-3-pyridinyl)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)-4,5-difluorobenzamide (0.300 g, 0.630 mmol), 27% aqueous ammonium hydroxide, and 2-(methyloxy)-4-(1-propyl-1,2,5,6-tetrahydro-3-pyridinyl)aniline (0.250 g, 0.950 mmol) and isolated as a yellow solid (0.040 g, 12% Yield); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.89 (t, J=7.14 Hz, 3H), 1.54 (s, 2H), 1.74 (s, 2H), 2.25 (s, 2H), 2.42 (s, 2H), 3.26 (s, 2H), 3.88 (s, 3H), 6.14 (s, 1H), 6.23-6.32 (m, 1H), 6.93 (d, J=7.69 Hz, 1H), 7.02 (s, 2H), 7.76 (s, 1H), 7.91 (dd, J=1.65, 0.92 Hz, 1H), 7.97 (dd, J=11.72, 8.79 Hz, 1H), 8.12 (d, J=8.42 Hz, 1H), 8.33 (s, 1H), 9.08 (dd, J=14.65, 7.69 Hz, 1H), 11.43 (s, 1H), 12.25 (s, 1H). ESI-MS (M+H) 533. Retention time 1.75 minutes.

Sources & evidence

ORD record
ord-0ed2e687268c47798b67c0de5a8f2b03
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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