Dicyclohexylcarbodiimide → tert-butyl-N-[1-[[5-bromo-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxo-propan-2-yl]-N-methylcarbamate

HRID 535387

반응식

HRID 535387 반응식
[CH3:1][N:2]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:3]([CH3:7])[C:4]([OH:6])=O.C1(N=C=NC2CCCCC2)CCCCC1.[Br:30][C:31]1[CH:32]=[CH:33][C:34]([NH2:45])=[N:35][C:36]=1[C:37]#[C:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(Cl)Cl>[C:11]([O:10][C:8](=[O:9])[N:2]([CH:3]([CH3:7])[C:4]([NH:45][C:34]1[CH:33]=[CH:32][C:31]([Br:30])=[C:36]([C:37]#[C:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[N:35]=1)=[O:6])[CH3:1])([CH3:14])([CH3:13])[CH3:12]

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 44368572-(((Tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 86694367HCID 86694367, 화합물

생성물 1

HCID 86694372tert-butyl-N-[1-[[5-bromo-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxo-propan-2-yl]-N-methylcarbamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

A mixture of 2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoic acid (36 g, 177 mmol) and N,N′-dicyclohexylcarbodiimide (22.5 g, 109 mmol) in DCM (150 ml) is stirred with ice bath cooling for 30 minutes. A solution of 5-bromo-6-(2-phenylethynyl)pyridin-2-amine B2a (20 g, 73.2 mmol) in DCM (100 ml) is added. After stirring for 7 days at RT the reaction mixture is diluted with DCM and extracted with water. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by NP chromatography. Yield: 25 g (74%). HPLC-MS: M+H=458/460; tR=2.33 min (*Method—1).

후처리

  1. temperaturecooling for 30 minutes
  2. stirringAfter stirring for 7 days at RT the reaction mixture
  3. extractionextracted with water
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe product is purified by NP chromatography

출처 및 근거

ORD 기록
ord-d0dda53cdc214083ae398d2e611f12cf
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859541B2

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