Diisopropylethylamine → HCID 20694720, 화합물

HRID 380662노트

반응식

HRID 380662 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2N=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH3:45][N:46]([CH3:63])[NH:47][C:48]([C:50]1([CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1)=[O:49].C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C)C=O>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[C:10]([N:53]1[CH2:54][CH2:55][C:50]([CH2:56][C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)([C:48]([NH:47][N:46]([CH3:63])[CH3:45])=[O:49])[CH2:51][CH2:52]1)=[O:12])([CH3:2])([CH3:3])[CH3:4]

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 333429Stk367969HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20694706HCID 20694706, 화합물

생성물 1

HCID 20694720HCID 20694720, 화합물수율 78.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-tert-butoxycarbonylamino-3-(1H-indole-3-yl)propionic acid (0.37 g, 1.2 mmol) in methylene chloride (15 ml) and dimethylformamid (5 ml) was added 1-hydroxy-7-azabenzotriazole (0.16 mg, 1.20 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.23 9, 1.20 mmol) and the mixture was stirred for 30 min. Then 4-benzylpiperidine-4-carboxylic acid N′,N′-dimethylhydrazide (0.26g, 1.0 mmol) and diisopropylethylamine (0.69 ml, 4.0 mmol) was added and the mixture was stirred overnight. Methylene chloride (100 ml) was added and the mixture was washed with saturated aqueous sodium hydrogencarbonate (20 ml), water (20 ml), dried (MgSO4), filtered and concentrated in vacuo. The obtained oil was chromatographed on silica (40 g) with methylene chloride/(10% ammonia in methanol) (9:1) to give 0.43 g of (2-(4-benzyl-4-(N′,N′-dimethylhydrazinocarbonyl)piperidine-1-yl)-1-(1H-indole-3-ylmethyl)-2-oxoethyl)carbamic acid tert-butyl ester as a colorless oil.

후처리

  1. stirringthe mixture was stirred overnight
  2. washthe mixture was washed with saturated aqueous sodium hydrogencarbonate (20 ml), water (20 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe obtained oil was chromatographed on silica (40 g) with methylene chloride/(10% ammonia in methanol) (9:1)

출처 및 근거

ORD 기록
ord-9f698c795b0e4d3b80fe2b54db917e67
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303620B1

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