Acetonitrile → HCID 178501358, 화합물

HRID 535093

반응식

HRID 535093 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C@H:17]3[CH2:22][CH2:21][NH:20][CH2:19][C@@H:18]3[C:23]([O:25][CH3:26])=[O:24])=[O:16])[CH2:11][CH2:10]2)=[C:5]([CH3:27])[CH:4]=1)#[N:2].C(#N)C.C(N(CC)CC)C.[CH:38]1[CH:43]=[CH:42][C:41]([O:44][C:45](OC2C=CC=CC=2)=[N:46][C:47]#[N:48])=[CH:40][CH:39]=1>>[C:47](/[N:46]=[C:45](\[O:44][C:41]1[CH:42]=[CH:43][CH:38]=[CH:39][CH:40]=1)/[N:20]1[CH2:21][CH2:22][C@H:17]([C:15]([N:12]2[CH2:13][CH2:14][N:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=3[CH3:27])[CH2:10][CH2:11]2)=[O:16])[C@@H:18]([C:23]([O:25][CH3:26])=[O:24])[CH2:19]1)#[N:48]

참가 물질

5

반응물 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 688090Diphenyl N-CyanocarbonimidateHCID 67304591Methyl(3r,4s)-4-[4-(4-cyano-2-methylphenyl)piperazin-1-yl]carbonylpiperidine-3-carboxylate

생성물 1

HCID 178501358HCID 178501358, 화합물

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온도
85 °C

실험 절차

To a stirred solution of methyl (3R,4S)-4-[4-(4-cyano-2-methylphenyl)piperazin-1-yl]carbonylpiperidine-3-carboxylate (386.500 mg, 1.04334E-3 mol) in anhydrous acetonitrile (6.000 mL, 0.1149 mol) at rt was added triethylamine (0.2923 mL, 0.002087 mol) and diphenyl cyanocarbonimidate (384.4 mg, 0.001565 mol). The reaction mixture was heated to reflux (oil bath temperature: 85° C.) for 5 hrs. The reaction mixture was concentrated in vacuo. The residue was purified by Combiflash with 40-90% EtOAc/Hex to give the product (60% in yield). MS (ESI): (M+H)+=515.

후처리

  1. temperatureThe reaction mixture was heated
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by Combiflash with 40-90% EtOAc/Hex
  4. customto give
  5. customthe product (60% in yield)

출처 및 근거

ORD 기록
ord-09384e60a2364b2b979605f8df44b6ee
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853243B2

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