Maleic Acid → HCID 178488179, compound

HRID 898012Notes

Reaction equation

HRID 898012 reaction equation
C(O)(=O)C.C(O)(=O)C.[NH2:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]2[N:16]([CH:40]3[CH2:45][CH2:44][N:43]([CH2:46][C:47]4[N:48]=[CH:49][NH:50][CH:51]=4)[CH2:42][CH2:41]3)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]4[N:29]([CH3:37])[C:30]5[C:35]([CH:36]=4)=[CH:34][CH:33]=[CH:32][CH:31]=5)=[O:27])=[C:21]([O:38][CH3:39])[CH:20]=3)[C:11]=12.[C:52]([OH:59])(=[O:58])/[CH:53]=[CH:54]\[C:55]([OH:57])=[O:56]>C(OCC)(=O)C.C(O)C>[C:52]([OH:59])(=[O:58])/[CH:53]=[CH:54]\[C:55]([OH:57])=[O:56].[C:52]([OH:59])(=[O:58])/[CH:53]=[CH:54]\[C:55]([OH:57])=[O:56].[NH2:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]2[N:16]([CH:40]3[CH2:45][CH2:44][N:43]([CH2:46][C:47]4[N:48]=[CH:49][NH:50][CH:51]=4)[CH2:42][CH2:41]3)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]4[N:29]([CH3:37])[C:30]5[C:35]([CH:36]=4)=[CH:34][CH:33]=[CH:32][CH:31]=5)=[O:27])=[C:21]([O:38][CH3:39])[CH:20]=3)[C:11]=12

Participants

5

Reactant 2

HCID 444266Maleic AcidHCID 178476568HCID 178476568, compound

Product 1

HCID 178488179HCID 178488179, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 702EthanolCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

N2-(4-{4-amino-1-[1-(1H-4-imidazolylmethyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-1-methyl-1H-2-indolecarboxamide, diacetate salt (170 mg, 0.244 mmol) was dissolved in hot ethyl acetate (25 mL) and a few drops of ethanol. Maleic acid (103 mg, 0.884 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 N2-(4-{4-amino-1-[1-(1H-4-imidazolylmethyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-1-methyl-1H-2-indolecarboxamide, dimaleate salt (153 mg, 76%). 1H NMR (DMSO-d6) δ 2.19 (m, 2H), 2.49 (m, 2H), 3.19 (m, 2H), 3.52 (m, 2H), 3.96 (s, 3H), 4.04 (s, 3H), 4.21 (s, 2H), 5.02 (m, 1H), 6.15 (s, 4H), 7.16 (m, 1H), 7.32 (m, 5H), 7.40 (s, 1H), 7.59 (d, J=8.45 Hz, 1H), 7.71 (d, J=7.95 Hz, 1H), 7.98 (bs, 1H), 8.13 (d, J=8.16 Hz, 1H), 8.27 (s, 1H), 9.44 (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.): RT=1.98 min. MH+=577.3.

Workup

  1. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-99d965aa7dc148819098392a2fc724b8
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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