Maleic Acid → N2-{4-[4-amino-1-(2-morpholinoethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-1-methyl-1H-2-indolecarboxamide dimaleate

HRID 897836ノート

反応式

HRID 897836 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]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:40]([OH:47])(=[O:46])/[CH:41]=[CH:42]\[C:43]([OH:45])=[O:44]>C(OCC)(=O)C>[C:40]([OH:47])(=[O:46])/[CH:41]=[CH:42]\[C:43]([OH:45])=[O:44].[C:40]([OH:47])(=[O:46])/[CH:41]=[CH:42]\[C:43]([OH:45])=[O:44].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]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 22347049N2-{4-[4-amino-1-(2-morpholinoethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-1-methyl-1H-2-indolecarboxamide

生成物 1

HCID 86586281N2-{4-[4-amino-1-(2-morpholinoethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-1-methyl-1H-2-indolecarboxamide dimaleate収率 43.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a mixture of N2-{4-[4-amino-1-(2-morpholinoethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-1-methyl-1H-2-indolecarboxamide (0.048 g, 0.091 mmol) in warm ethyl acetate (2 mL) was added a solution of maleic acid (0.021 g, 0.18 mmol) in warm ethyl acetate (1 mL). A precipitate formed immediately. The reaction mixture was allowed to cool to ambient temperature and the precipitate was collected by filtration, washed with ethyl acetate (5 mL), and dried in vacuo to afford N2-{4-[4-amino-1-(2-morpholinoethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-1-methyl-1H-2-indolecarboxamide dimaleate as a light brown solid (0.030 g, 0.039 mmol): 1H NMR (d6-DMSO, 400 MHz): δH 9.45 (1H, s), 8.31 (1H, s), 8.15 (1H, d, J=8.0 Hz), 7.71 (1H, d, J=8.0 Hz), 7.59 (1H, d, J=8.4 Hz), 7.31-7.35 (4H, m), 7.16 (1H, t, J=7.4 Hz), 6.17 (4H, s), 4.72-4.73 (2H, m), 4.04 (3H, s), 3.96 (3H, s), 3.72-3.79 (4H, m), and 3.10-3.30 (6H, obscured by water peak); RP-HPLC (Hypersil C18, 5 μm 100 Å, 15 cm; 5%-100% acetonitrile-0.1 M ammonium acetate over 15 min, 1 mL/min). Rt 11.08 min. MS: M+527.3.

後処理

  1. customA precipitate formed immediately
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with ethyl acetate (5 mL)
  4. customdried in vacuo

出典と根拠

ORDレコード
ord-cb6e580511e84d26a0ad8f3ec19bd34d
出典データセット
uspto-grants-2005_07
特許番号
US06921763B2

反応ノート

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