Diisopropylcarbodiimide → {3-[6-[(4-tert-Butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]-1,2,4-oxadiazol-5-yl}methanol

HRID 1691449노트

반응식

HRID 1691449 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([C:25](=[N:27][OH:28])[NH2:26])[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:29]=[C:30]([C:33]([F:36])([F:35])[F:34])[CH:31]=[CH:32][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:37]([O:44]CC(O)=O)[C:38]1C=CC=CC=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C>C(Cl)Cl.CCOC(C)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([C:25]4[N:26]=[C:38]([CH2:37][OH:44])[O:28][N:27]=4)[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:29]=[C:30]([C:33]([F:35])([F:36])[F:34])[CH:31]=[CH:32][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

8

반응물 5

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 290301(Benzyloxy)acetic acidHCID 866490386-[(4-tert-Butylphenyl)sulfonyl]-N'-hydroxy-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carboximidamide2회

생성물 1

HCID 59618782{3-[6-[(4-tert-Butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]-1,2,4-oxadiazol-5-yl}methanol

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 6-[(4-tert-butylphenyl)sulfonyl]-N′-hydroxy-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carboximidamide (intermediate 55, 0.20 g, 0.38 mmol), 2-benzyloxyacetic acid (0.064 mg, 0.385 mmol), DIPEA (0.103 mg, 0.800 mmol), HOBt (0.108 g, 0.8 mmol), and DIC (0.073 g, 0.578 mmol) in DCM (3.85 mL) was stirred at rt for 4 h. The reaction mixture was diluted with EtOAc, washed with dilute NaOH, 5% citric acid, dried (MgSO4) and concentrated to afford the desired product, which was used without further purification. LC/MS: m/e 667.5 (M+H)+.

후처리

  1. washwashed with dilute NaOH, 5% citric acid
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ed157ceba7c34b7c92947a636b4b2b9d
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153626B2

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