Diisopropylethylamine → 5-{1-[(5-chloro-2-fluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 1910024노트

반응식

HRID 1910024 반응식
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:19]4[C:18]([NH2:20])=[N:17][CH:16]=[N:15][C:14]=4[N:13]([CH3:21])[CH:12]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([F:33])=[C:27]([CH2:29][C:30](O)=[O:31])[CH:28]=1.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[CH:24]=[CH:25][C:26]([F:33])=[C:27]([CH2:29][C:30]([N:2]2[C:10]3[C:5](=[CH:6][C:7]([C:11]4[C:19]5[C:18]([NH2:20])=[N:17][CH:16]=[N:15][C:14]=5[N:13]([CH3:21])[CH:12]=4)=[CH:8][CH:9]=3)[CH2:4][CH2:3]2)=[O:31])[CH:28]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 27737235-Chloro-2-fluorophenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668238195-(2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine HCl

생성물 1

HCID 668236225-{1-[(5-chloro-2-fluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

In a 20 mL vial with cap, to the solution of 5-(2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine HCl (70 mg, 0.232 mmol), (5-chloro-2-fluorophenyl)acetic acid (44.2 mg, 0.234 mmol), and HATU (89 mg, 0.234 mmol) in DMF (2 mL) was added Hunig's base (0.162 mL, 0.928 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=436.4 [M+H]+ 1H NMR (400 MHz, DMSO-d6) δ ppm 3.22-3.30 (m, 2H), 3.74 (s, 3H), 3.96 (s, 2H), 4.25-4.32 (m, 2H), 7.21-7.28 (m, 2H), 7.30 (s, 1H), 7.33 (s, 1H), 7.39-7.44 (m, 1H), 7.47 (dd, J=6.32, 2.78 Hz, 1H), 8.08 (d, J=8.34 Hz, 1H), 8.15 (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-a0b87c77829e4ad6b581f6a082f00da1
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598156B2

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