Ammonium Hydroxide → 2-{[2-({1-[3-(dimethylamino)propanoyl]-6-methoxy-1,2,3,4-tetrahydroquinolin-7-yl}amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}-6-fluorobenzamide

HRID 1014522Notes

Reaction equation

HRID 1014522 reaction equation
[CH3:1][N:2]([CH3:41])[CH2:3][CH2:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([O:39][CH3:40])=[C:14]([NH:17][C:18]3[NH:23][C:22]4=[N:24][CH:25]=[CH:26][C:21]4=[C:20]([NH:27][C:28]4[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:29]=4[C:30]([NH:32]C)=[O:31])[N:19]=3)[CH:15]=2)[CH2:10][CH2:9][CH2:8]1)=[O:6].ClC1N=C(NC2C=CC=C(F)C=2C(N)=O)C2C=CN(S(C3C=CC(C)=CC=3)(=O)=O)C=2N=1.[OH-].[NH4+].CN(C)CCC(N1C2C(=CC(OC)=C(N)C=2)CCC1)=O>>[CH3:41][N:2]([CH3:1])[CH2:3][CH2:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([O:39][CH3:40])=[C:14]([NH:17][C:18]3[NH:23][C:22]4=[N:24][CH:25]=[CH:26][C:21]4=[C:20]([NH:27][C:28]4[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:29]=4[C:30]([NH2:32])=[O:31])[N:19]=3)[CH:15]=2)[CH2:10][CH2:9][CH2:8]1)=[O:6]

Participants

5

Reactant 4

HCID 14923Ammonium HydroxideHCID 594420021-[3-(Dimethylamino)propanoyl]-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinamineHCID 866441882-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzamideHCID 1784855222-[(2-{[1-(N,N-dimethyl-beta-alanyl)-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinyl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-6-fluoro-N-methylbenzamide

Product 1

HCID 1784864712-{[2-({1-[3-(dimethylamino)propanoyl]-6-methoxy-1,2,3,4-tetrahydroquinolin-7-yl}amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}-6-fluorobenzamide

Procedure

According to General Protocol III, 2-[(2-{[1-(N,N-dimethyl-β-alanyl)-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinyl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-6-fluoro-N-methylbenzamide (0.043 g) was prepared from 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzamide (0.15 g, 0.33 mmol), 27% aqueous ammonium hydroxide, and 1-[3-(dimethylamino)propanoyl]-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinamine (0.12 g, 0.42 mmol). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.80-1.90 (m, 2 H), 1.97-2.08 (bs, 6 H), 2.53-2.59 (m, signal underneath DMSO, 2 H), 2.63-2.71 (m, 2 H), 2.73-2.83 (m, 2 H), 3.68 (m, 2 H), 3.86 (s, 3 H), 6.27 (s, 1 H), 6.83-6.88 (m, 1 H), 6.90-6.98 (m, 1 H), 7.00-7.05 (m, 1 H), 7.39-7.48 (m, 1 H), 7.56 (s, 1 H), 8.00-8.11 (m, 2 H), 8.31 (s, 1 H), 8.45 (d, J=7.7 Hz, 1 H), 10.47 (s, 1 H), 11.82 (bs, 1 H); ESIMS (M+H)+=547.

Sources & evidence

ORD record
ord-0d41a5fccaf743ab956be458e7acaca2
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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