Maleic Acid → HCID 178488206、化合物

HRID 897568

反応式

HRID 897568 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:32]3[CH2:37][CH2:36][C@H:35]([N:38]4[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]4)[CH2:34][CH2:33]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)[C:3]=12.[C:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]\[C:48]([OH:50])=[O:49]>C(OCC)(=O)C>[C:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]\[C:48]([OH:50])=[O:49].[C:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]\[C:48]([OH:50])=[O:49].[C:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]\[C:48]([OH:50])=[O:49].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:32]3[CH2:33][CH2:34][C@H:35]([N:38]4[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]4)[CH2:36][CH2:37]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)[C:3]=12

参加物

4

反応物 2

HCID 444266Maleic AcidHCID 178488203HCID 178488203、化合物

生成物 1

HCID 178488206HCID 178488206、化合物

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

trans-N2-(4-{4-Amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-1-methyl-1H-2-indolecarboxamide (545 mg, 0.917 mmol) was dissolved in hot ethyl acetate (60 mL) and maleic acid (320 mg, 2.75 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 trans-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-1-methyl-1H-2-indolecarboxamide, dimaleate salt (473 mg). 1H NMR (DMSO-d6) δ 1.60 (m, 2H), 2.06 (m, 6H), 2.68 (s, 3H), 2.83-3.57 (bm, 9H), 3.96 (s, 3H), 4.04 (s, 3H), 4.72 (m, 1H), 6.18 (s, 6H), 7.16 (m, 1H), 7.28-7.36 (m, 4H), 7.59 (d, J=8.44 Hz, 1H), 7.72 (d, J=7.94 Hz, 1H), 8.13 (d, J=8.15, 1H), 8.28 (s, 1H), 9.44 (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+=594.4, Rt=2.24.

後処理

  1. filtrationThe solid was collected by filtration to trans-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-1-methyl-1H-2-indolecarboxamide, dimaleate salt (473 mg)
  2. waitEluents: 0% B/A to 100% B/A in 4 min. (B

出典と根拠

ORDレコード
ord-daa212b62124408b9f37f4ddd7e8b047
出典データセット
uspto-grants-2005_07
特許番号
US06921763B2

関連ノート

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