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p-Toluenesulfonic acid monohydrate → 5-chloro-N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methylindol-3-yl)pyrimidin-2-amine

HRID 1842743
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HRID 1842743 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH3:17])[CH:9]=2)[C:5]([Cl:18])=[CH:4][N:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[F:31][C:32]1[C:38]([N+:39]([O-:41])=[O:40])=[CH:37][C:35]([NH2:36])=[C:34]([O:42][CH3:43])[CH:33]=1>CC(O)CCC>[Cl:18][C:5]1[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH3:17])[CH:9]=2)=[N:7][C:2]([NH:36][C:35]2[CH:37]=[C:38]([N+:39]([O-:41])=[O:40])[C:32]([F:31])=[CH:33][C:34]=2[O:42][CH3:43])=[N:3][CH:4]=1
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참가 물질

5

반응물 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 574290724-Fluoro-2-methoxy-5-nitroaniline2회HCID 580714413-(2,5-Dichloropyrimidin-4-yl)-1-methyl-1H-indole2회

생성물 1

HCID 712392825-chloro-N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methylindol-3-yl)pyrimidin-2-amine수율 72.2%

시약·촉매·용매 1

HCID 22386
2-Pentanol
용매

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온도
125 °C

실험 절차

A mixture of 3-(2,5-dichloropyrimidin-4-yl)-1-methylindole (Intermediate 88, 1281 mg, 4.60 mmol), p-toluene sulphonic acid monohydrate (964 mg, 5.07 mmol) and 4-fluoro-2-s methoxy-5-nitroaniline (Intermediate 23, 900 mg, 4.84 mmol) in 2-pentanol (50 mL) was heated at 125° C. for 18 h. A precipitate formed from the solution upon cooling. The precipitate was collected by filtration, washed with CH3OH (10 mL) and diethyl ether (20 mL) and dried on the filter to give the title compound (1.42 g, 72%) as a tan solid, which was used without further purification; 1H NMR: 3.91 (3H, s), 3.96 (3H, s), 7.05 (1H, t), 7.23-7.3 (1H, m), 7.39 (1H, d), 7.53 (1H, d), 8.33 (1H, d), 8.47 (1H, s), 8.58 (1H, s), 8.65 (1H, d), 8.76 (1H, s); m/z: ES+ MH+ 428.10.

후처리

  1. customA precipitate formed from the solution
  2. temperatureupon cooling
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with CH3OH (10 mL) and diethyl ether (20 mL)
  5. customdried on the
  6. filtrationfilter

출처 및 근거

ORD 기록
ord-7c385ee35133423b8d49db771377d6cb
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08946235B2

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