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 1910036노트

반응식

HRID 1910036 반응식
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]

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-f7f31fa5b85849d2b8cecd6fa607cd3f
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598156B2

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