Maleic Acid → HCID 178488211, compound

HRID 897701Notes

Reaction equation

HRID 897701 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:31]3[CH2:36][CH2:35][C@H:34]([N:37]4[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]4)[CH2:33][CH2:32]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[O:24][C:23]5[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=5[CH:21]=4)=[O:19])=[C:13]([O:29][CH3:30])[CH:12]=3)[C:3]=12.[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:44]([OH:51])(=[O:50])/[CH:45]=[CH:46]\[C:47]([OH:49])=[O:48].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:31]3[CH2:36][CH2:35][C@H:34]([N:37]4[CH2:38][CH2:39][N:40]([CH3:43])[CH2:41][CH2:42]4)[CH2:33][CH2:32]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[O:24][C:23]5[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=5[CH:21]=4)=[O:19])=[C:13]([O:29][CH3:30])[CH:12]=3)[C:3]=12

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 178488210HCID 178488210, compound

Product 1

HCID 178488211HCID 178488211, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

trans-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)benzo[b]furan-2-carboxamide (497 mg, 0.855 mmol) was dissolved in hot ethyl acetate (56 mL) and maleic acid (298 mg, 2.566 mmol) in hot ethyl acetate (5 mL) was added. The reaction mixture was stirred at room temperature for 5 hours. The solid was collected by filtration to give trans-N2-(4-{4-Amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)benzo[b]furan-2-carboxamide, trimaleate salt (117 mg, 92%). 1H NMR (DMSO-d6) δ 1.60 (m, 2H), 2.09 (m, 6H), 2.68 (s, 3H), 2.82-3.17 (bm, 9H), 4.00 (s, 3H), 4.69 (m, 1H), 6.16 (s, 6H), 7.30-7.42 (m, 3H), 7.54 (m, 1H), 7.76-7.85 (m, 3H), 8.25 (m, 2H), 9.51 (s, 1H); LCMS (Finigan-Column: Pecophere, 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+=581.4, Rt=2.12 min.

Workup

  1. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-2b29e4b1ef064fdeaf8c3e2f8adab63e
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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