Water → N1-(2-(Dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(4-(1-methyl-1H-indol-3-yl)-2-pyrimidinyl)-2-nitro-1,4-benzenediamine

HRID 1842826노트

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HRID 1842826 반응식
F[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([NH:11][C:12]2[N:17]=[C:16]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH3:27])[CH:19]=3)[CH:15]=[CH:14][N:13]=2)=[C:4]([O:28][CH3:29])[CH:3]=1.[CH3:30][NH:31][CH2:32][CH2:33][N:34]([CH3:36])[CH3:35].C(N(C(C)C)C(C)C)C.O>CC(N(C)C)=O>[CH3:35][N:34]([CH3:36])[CH2:33][CH2:32][N:31]([CH3:30])[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([NH:11][C:12]2[N:17]=[C:16]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH3:27])[CH:19]=3)[CH:15]=[CH:14][N:13]=2)=[C:4]([O:28][CH3:29])[CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 81531DiisopropylethylamineHCID 71239058N-(4-fluoro-2-Methoxy-5-nitrophenyl)-4-(1-Methylindol-3-yl)pyriMidin-2-aMine2회

생성물 1

HCID 71239349N1-(2-(Dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(4-(1-methyl-1H-indol-3-yl)-2-pyrimidinyl)-2-nitro-1,4-benzenediamine수율 104.2%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
85 °C

실험 절차

To a stirred solution of N-(4-fluoro-2-methoxy-5-nitro-phenyl)-4-(1-methylindol-3-yl)pyrimidin-2-amine (Intermediate 176, 65 g, 160.28 mmol) and N,N′,N′-trimethylethane-1,2-diamine (19.65 g, 192.3 mmol) in DMA (630 mL) was added N-ethyl-N-isopropyl-propan-2-amine (26.93 g, 208.4 mmol) at r.t. The resulting mixture was stirred at 85° C. for 5-6 h then cooled to r.t. Water (630 mL) was then added and the mixture was stirred for 3-4 h. Solid material was collected by filtration, washed with water (315 mL) and dried at 50° C. for 12 h to give the title compound (79.4 g, 96%) as orange solid; 1H NMR (CDCl3): 2.29 (6H, s) 2.60 (2H, t), 2.93 (3H, s), 3.31 (2H, t), 3.96 (3H, s), 4.00 (3H, s), 6.69 (1H, s), 7.21 (1H, d), 7.30-7.38 (2H, m), 7.43 (1H, d), 7.56 (1H, s), 8.18 (1H, d), 8.30 (1H, s), 8.41 (1H, d), 9.59 (1H, s); m/z: ES+ MH+ 476.23.

후처리

  1. temperaturethen cooled to r.t
  2. stirringthe mixture was stirred for 3-4 h
  3. filtrationSolid material was collected by filtration
  4. washwashed with water (315 mL)
  5. customdried at 50° C. for 12 h

출처 및 근거

ORD 기록
ord-930b4222245f406eb3ceef4a09f45bd1
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946235B2

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