Triethylamine → HCID 67796126, 화합물

HRID 1655009노트

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HRID 1655009 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:14])[NH:10][CH2:11][C:12]=2[OH:13])[CH:5]=[CH:6][CH:7]=1.C(N([CH2:20][CH3:21])CC)C.ClC(Cl)(O[C:26](=[O:32])OC(Cl)(Cl)Cl)Cl.[NH2:34][C@@H:35]1[N:41]=[C:40](C2CCCCC2)[C:39]2[CH:48]=[CH:49][CH:50]=[CH:51][C:38]=2[N:37]([CH3:52])[C:36]1=[O:53]>O1CCCC1>[CH2:21]1[CH2:20][CH:6]([C@@:35]2([NH:34][C:26]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([C:8]4[C:9](=[O:14])[NH:10][CH2:11][C:12]=4[OH:13])[CH:3]=3)=[O:32])[N:41]=[CH:40][C:39]3[CH:48]=[CH:49][CH:50]=[CH:51][C:38]=3[N:37]([CH3:52])[C:36]2=[O:53])[CH2:7][CH2:2][CH2:3]1

참가 물질

6

반응물 4

HCID 8471Triethylamine2회HCID 94429TriphosgeneHCID 18656025HCID 18656025, 화합물HCID 547073163-(3-Aminophenyl)-1,5-dihydro-4-hydroxy-2H-pyrrol-2-one

생성물 1

HCID 67796126HCID 67796126, 화합물수율 40.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

3-(3-Aminophenyl)-1,5-dihydro-4-hydroxy-2H-pyrrol-2-one (409 mg, 2.15 mmol) was suspended in anhydrous tetrahydrofuran (40 ml), under an atmosphere of nitrogen. Triethylamine (296 μl, 2.14 mmol) was then added dropwise over rain and the mixture stirred for a further 2 min. The mixture was then cooled to 0° C. and triphosgene (210 mg, 0.71 mmol) was added and the mixture stirred for 2 min. Triethylamine (595 μl, 4.3 mmol) was then added over a 5 min period and the mixture stirred at 0° C. for a further 5 min. The cooling bath was removed and the mixture stirred at ambient temperature for 10 min. The mixture was then cooled back to 0° C. and a solution of (R)-amino-5-cyclohexyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (400 mg, 1.47 mmol) in anhydrous tetrahydrofuran (5 ml) was added dropwise. The mixture was stirred at 0° C. for 5 rain then allowed to warm to room temperature and stirred for 30 min. The residue was then evaporated in vacuo and the residue chromatographed on silica gel, using 94:6:0.6 dichloromethane:methanol:acetic acid as the eluant. The title compound (140 mg, 20%) was isolated as a white solid. mp 220° C. (dec.). 1H NMR (360MHz, D6 -DMSO) δ0.90 (1H, m), 1.09-1.91 (9H, m), 2.93 (1H, m), 3.32 (3H, s), 3.82 (2H, s), 5.07 (1H, d, J=8Hz), 7.13 (1H, t, J=8Hz), 7.23 (1H, d, J =8Hz), 7.35-7.39 (2H, m), 7.53-7.65 (3H, m), 7.74 (1H, d, J=8Hz), 7.85 (1H, s), 8.97 (1H, s).

후처리

  1. stirringthe mixture stirred for 2 min
  2. stirringthe mixture stirred at 0° C. for a further 5 min
  3. customThe cooling bath was removed
  4. stirringthe mixture stirred at ambient temperature for 10 min
  5. temperatureThe mixture was then cooled back to 0° C.
  6. stirringThe mixture was stirred at 0° C. for 5 rain
  7. temperatureto warm to room temperature
  8. stirringstirred for 30 min
  9. customThe residue was then evaporated in vacuo
  10. customthe residue chromatographed on silica gel

출처 및 근거

ORD 기록
ord-e24a1a9ea3864c02a98d69d7a911e67d
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05410049

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