Maleic Acid → HCID 178488196, compound

HRID 897699Notes

Reaction equation

HRID 897699 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-6d6fe39b6f3a4052880c0b94fd10f5c8
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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