Diisopropylethylamine → tert-Butyl 3-({6-[(tert-butoxycarbonyl)amino]-5-(trifluoroacetyl)pyridin-2-yl}amino)piperidine-1-carboxylate

HRID 57692

반응식

HRID 57692 반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.Cl[C:16]1[N:21]=[C:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([C:30](=[O:35])[C:31]([F:34])([F:33])[F:32])=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.C(OCC)(=O)C>[C:25]([O:24][C:23]([NH:22][C:20]1[N:21]=[C:16]([NH:1][CH:2]2[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]2)[CH:17]=[CH:18][C:19]=1[C:30](=[O:35])[C:31]([F:32])([F:33])[F:34])=[O:29])([CH3:28])([CH3:26])[CH3:27]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 5458091-BOC-3-AminopiperidineHCID 57911758tert-Butyl[6-chloro-3-(trifluoroacetyl)pyridin-2-yl]carbamate

생성물 1

HCID 57911775tert-Butyl 3-({6-[(tert-butoxycarbonyl)amino]-5-(trifluoroacetyl)pyridin-2-yl}amino)piperidine-1-carboxylate

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

561 mg (2.8 mmol) of tert-butyl 3-aminopiperidine-1-carboxylate, 700 mg (2.16 mmol) of tert-butyl [6-chloro-3-(trifluoroacetyl)pyridin-2-yl]carbamate (Example 32A) and 0.56 ml (3.23 mmol) of diisopropylethylamine were suspended in 14 ml of DMSO and heated in a microwave reactor at 90° C. for 45 min. The reaction mixture was diluted with ethyl acetate (100 ml) and washed with saturated aqueous ammonium chloride solution (three times 40 ml) and then saturated aqueous sodium bicarbonate solution (40 ml). The organic phase was dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1 to 1:1). This gave 670 mg (63% of theory) of the product.

후처리

  1. washwashed with saturated aqueous ammonium chloride solution (three times 40 ml)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1 to 1:1)

출처 및 근거

ORD 기록
ord-29e8997d475147c58d94b2780b9537e0
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434731B2

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