4-Methylpyrazole → {2-Chloro-9-[(1R,4S)-4-(4-methyl-pyrazol-1-yl)-cyclopent-2-enyl]-9H-purin-6-yl}-(2,2-diphenyl-ethyl)-amine

HRID 1641886노트

반응식

HRID 1641886 반응식
C(OC(=O)O[C@H:6]1[CH2:10][C@@H:9]([N:11]2[CH:19]=[N:18][C:17]3[C:12]2=[N:13][C:14]([Cl:35])=[N:15][C:16]=3[NH:20][CH2:21][CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:8]=[CH:7]1)C.[CH3:37][C:38]1[CH:39]=[N:40][NH:41][CH:42]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[Cl:35][C:14]1[N:13]=[C:12]2[C:17]([N:18]=[CH:19][N:11]2[C@@H:9]2[CH2:10][C@H:6]([N:40]3[CH:39]=[C:38]([CH3:37])[CH:42]=[N:41]3)[CH:7]=[CH:8]2)=[C:16]([NH:20][CH2:21][CH:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:15]=1

참가 물질

4

반응물 3

HCID 34064-MethylpyrazoleHCID 11776TriphenylphosphineHCID 86622637Carbonic acid (1S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopent-2-enyl ester ethyl ester

생성물 1

HCID 86622799{2-Chloro-9-[(1R,4S)-4-(4-methyl-pyrazol-1-yl)-cyclopent-2-enyl]-9H-purin-6-yl}-(2,2-diphenyl-ethyl)-amine

실험 절차

Carbonic acid (1S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopent-2-enyl ester ethyl ester (Intermediate AA) (2.00 g, 3.97 mmol) is placed in an oven-dried flask under an atmosphere of argon. Dry deoxygenated THF (20 mL) is added followed by 4-methyl-pyrazole (0.36 g, 4.37 mmol) and triphenylphosphine (0.16 g, 0.60 mmol). Tetrakis(triphenyl-phosphine)palladium(0) (0.23 g, 0.20 mmol) is then added and the reaction mixture is stirred at room temperature for 18 hours. The solvent is removed in vacuo and the title compound is obtained after purification by flash column chromatography (silica, iso-hexane/ethyl acetate 1:2). 1H nmr (CDCl3, 400 MHz); 8.10 (br s, 1H), 7.35-7.15 (m, 12H), 6.25 (m, 1H), 6.10 (m, 1H), 5.80 (m, 1H), 5.70 (m, 1H), 5.35 (m, 1H), 4.35 (t, 1H), 4.25 (m, 2H), 3.25 (m, 1H), 2.20 (m, 1H), 2.05 (s, 3H), MS (ES+) m/e 496 (MH+).

후처리

  1. customDry
  2. customdeoxygenated THF (20 mL)
  3. additionis added
  4. customThe solvent is removed in vacuo

출처 및 근거

ORD 기록
ord-7a15f8dd5f544734a22f1b73e3bb3745
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114877B2

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