Maleic Acid → HCID 178488196, compound

HRID 432410Notes

Reaction equation

HRID 432410 reaction equation
[C:1]1([C@@H:7]([CH3:43])[CH2:8][NH:9][C:10](=[O:42])[C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:25]4[C:20](=[N:21][CH:22]=[N:23][C:24]=4[NH2:26])[N:19]([C@H:27]4[CH2:32][CH2:31][C@@H:30]([N:33]5[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]5)[CH2:29][CH2:28]4)[N:18]=3)=[CH:13][C:12]=2[O:40][CH3:41])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:44]([OH:51])(=[O:50])/[CH:45]=[CH:46]\[C:47]([OH:49])=[O:48]>C(OCC)(=O)C>[C:44]([OH:51])(=[O:50])/[CH:45]=[CH:46]\[C:47]([OH:49])=[O:48].[C:44]([OH:51])(=[O:50])/[CH:45]=[CH:46]\[C:47]([OH:49])=[O:48].[C:1]1([C@@H:7]([CH3:43])[CH2:8][NH:9][C:10](=[O:42])[C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:25]4[C:20](=[N:21][CH:22]=[N:23][C:24]=4[NH2:26])[N:19]([C@H:27]4[CH2:32][CH2:31][C@@H:30]([N:33]5[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]5)[CH2:29][CH2:28]4)[N:18]=3)=[CH:13][C:12]=2[O:40][CH3:41])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 178488194HCID 178488194, compound

Product 1

HCID 178488196HCID 178488196, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

cis-N1-[(2R)-2-Phenylpropyl]-4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxybenzamide (100 mg, 0.172 mmol) was dissolved in hot ethyl acetate (12 mL) and maleic acid (60 mg, 0.515 mmol) in hot ethyl acetate (3 mL) was added. The reaction mixture was stirred at room temperature for 5 hours. The solid was collected by filtration to give cis-N1-[(2R)-2-phenylpropyl]-4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxybenzamide, dimaleate salt (117 mg, 87%). 1H NMR (DMSO-d6) δ 1.25 (d, J=6.96, 3H), 1.73 (m, 42H), 2.09 (m, 2H), 2.26 (m, 2H), 2.71 (s, 3H), 2.74 (m, 2H), 2.85-3.70 (bm, 7H), 3.89 (s, 3H), 4.85 (m, 1H), 6.14 (s, 4H), 7.20 (m, 3H), 7.31 (d, J=4.33, 4H), 8.12 (d, J=8.17 Hz, 1H), 8.24 (s, 1H), 9.20 (s, 1H). LC/MS (Finigan-Column: Pecosphere, C18, 3 um, 33×4.6 mm. Eluents: 0% B/A to 100% B/A in 4 min. (B: acetonitrile, A: 50 mM ammonia acetate buffer, pH 4.5), 3.0 mL/min.): MH+ =583.4 Rt=2.14 min.

Workup

  1. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-b4dd9e67c303498ca824b6934560e63d
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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