Maleic Acid → HCID 131725044, compound

HRID 2056146Notes

Reaction equation

HRID 2056146 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:30])[C:19]4[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=4[F:29])=[C:13]([O:31][CH3:32])[CH:12]=3)[C:3]=12.[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43]>C(OCC)(=O)C>[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43].[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:30])[C:19]4[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:21][C:20]=4[F:29])=[C:13]([O:31][CH3:32])[CH:12]=3)[C:3]=12

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 22346947HCID 22346947, compound

Product 1

HCID 131725044HCID 131725044, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

N1-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-fluoro-4-(trifluoromethyl)benzamide (380 mg, 0.717 mmol) was dissolved in hot ethyl acetate (70 mL) and maleic acid (167 mg, 1.435 mmol) in hot ethyl acetate (3 mL) was added. The reaction mixture was stirred at room temperature for 3 hours. The solid was collected by filtration to give N1-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-fluoro-4-(trifluoromethyl) benzamide, dimaleate salt (489 mg, 90%). 1H NMR (DMSO-d6) δ 2.15 (m, 2H), 2.41 (m, 2H), 3.23 (m, 2H), 3.94 (s, 3H), 5.09 (m, 1H), 6.14 (m, s, 4H), 7.33 (m, 2H), 7.76 (m, 1H), 7.88 (m, 1H), 7.99 (m, 1H), 8.28 (s, 1H), 8.33 (m, 2H), 8.70 (bs, 1H), 9.92 (s, 1H). LCMS (Thermoquest AQA single Quad MS, Finnigan HPLC-Column: Genesis, C18, 3 um, 33×4.6 mm. Eluents: 30% B/A to 95% B/A in 4.5 min. (B: acetonitrile, A: 50 mM ammonia acetate buffer, pH 4.5), 0.8 mL/min.): MH+=530.2, Rt=2.03 min.

Workup

  1. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-5b13c3ca241d4071be3f88e1c6015d09
Source dataset
uspto-grants-2008_02
Patent number
US07332497B2

Reaction notes

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