Tetrahydrofuran → HCID 11713729, 화합물

HRID 1867617노트

반응식

HRID 1867617 반응식
[NH2:1][C@@H:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][C:20]([F:23])([F:22])[F:21])[C:3]1=[O:24].C(N(CC)CC)C.[O:32]=[C:33]1[NH:37][C:36]([C:38]#[N:39])=[CH:35][N:34]1[CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.[O:46]1CCC[CH2:47]1>>[C:38]([C:36]1[NH:37][C:33](=[O:32])[N:34]([CH:40]2[CH2:45][CH2:44][N:43]([C:47]([NH:1][C@@H:2]3[N:8]=[C:7]([C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:6]4[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=4[N:4]([CH2:19][C:20]([F:21])([F:23])[F:22])[C:3]3=[O:24])=[O:46])[CH2:42][CH2:41]2)[CH:35]=1)#[N:39]

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 8471Triethylamine2회HCID 10854086HCID 10854086, 화합물HCID 598565282-Oxo-1-piperidin-4-yl-2,3-dihydro-1H-imidazole-4-carbonitrile

생성물 1

HCID 11713729HCID 11713729, 화합물

실험 절차

(3R)-3-Amino-5-phenyl-1-(2,2,2-trifluoroethyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one (38 mg, 0.114 mmol) (Y.-J. Shi et al., Tetrahedron, 1999, 55, 909-918) and triethylamine (0.017 mL, 0.120 mmol) were added to a solution of p-nitrophenylchloroformate (23 mg, 0.114 mmol) in tetrahydrofuran (15 mL) at 0 oC. After 1 h, 2-oxo-1-piperidin-4-yl-2,3-dihydro-1H-imidazole-4-carbonitrile (23 mg, 0.120 mmol) and additional triethylamine (0.034 μL, 0.240 mmol) were added. The reaction warmed to ambient temperature and was then heated to 50 oC. After 2 h, the reaction was concentrated and then partitioned between dichloromethane and saturated sodium bicarbonate. The organics were washed with water, brine, and dried over magnesium sulfate. Purification by silica gel chromatography (100% dichloromethane→7% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound (40 mg). MS 552.195 (M+1)

후처리

  1. temperaturewas then heated to 50 oC
  2. waitAfter 2 h
  3. concentrationthe reaction was concentrated
  4. custompartitioned between dichloromethane and saturated sodium bicarbonate
  5. washThe organics were washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. customPurification by silica gel chromatography (100% dichloromethane→7% methanol {1% ammonium hydroxide}/dichloromethane)

출처 및 근거

ORD 기록
ord-1fbfb7b0e31f4068836619a2bd9baf60
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07632832B2

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