Diisopropylethylamine → 3-{1-[(3-chloro-2,4-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 1910036ノート

反応式

HRID 1910036 の反応式
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:19]4[C:14](=[N:15][CH:16]=[N:17][C:18]=4[NH2:20])[N:13]([CH3:21])[N:12]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[Cl:22][C:23]1[C:24]([F:34])=[C:25]([CH2:30][C:31](O)=[O:32])[CH:26]=[CH:27][C:28]=1[F:29].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Cl:22][C:23]1[C:24]([F:34])=[C:25]([CH2:30][C:31]([N:2]2[C:10]3[C:5](=[CH:6][C:7]([C:11]4[C:19]5[C:14](=[N:15][CH:16]=[N:17][C:18]=5[NH2:20])[N:13]([CH3:21])[N:12]=4)=[CH:8][CH:9]=3)[CH2:4][CH2:3]2)=[O:32])[CH:26]=[CH:27][C:28]=1[F:29]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 177508243-Chloro-2,4-difluorobenzeneacetic acidHCID 668238703-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine HCl

生成物 1

HCID 668237563-{1-[(3-chloro-2,4-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

In a 20 mL vial with cap, to a solution of 3-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine HCl (70 mg, 0.231 mmol), (3-chloro-2,4-difluorophenyl)acetic acid (47.8 mg 0.231 mmol), and HATU (88 mg, 0.231 mmol) in DMF (2 mL) was added Hunig's base (0.162 mL, 0.925 mmol). The mixture was stirred overnight. The reaction was poured into water (100 mL), and an off-white solid was formed. The solid was filtered, washed with water (10 mL), and dried to afford the title compound as an off-white solid. LC-MS (ES) m/z=455.4 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.24-3.31 (m, 2H), 3.94 (s, 3H), 4.03 (s, 2H), 4.32 (t, J=8.46 Hz, 2H), 7.30-7.36 (m, 1H), 7.39-7.46 (m, 2H), 7.54 (s, 1H), 8.14 (d, J=8.34 Hz, 1H), 8.25 (s, 1H).

後処理

  1. customan off-white solid was formed
  2. filtrationThe solid was filtered
  3. washwashed with water (10 mL)
  4. customdried

出典と根拠

ORDレコード
ord-f7f31fa5b85849d2b8cecd6fa607cd3f
出典データセット
uspto-grants-2013_12
特許番号
US08598156B2

反応ノート

読み込み中…