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

HRID 535387

反応式

HRID 535387 の反応式
[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]

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 44368572-(((Tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 86694367HCID 86694367、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d0dda53cdc214083ae398d2e611f12cf
出典データセット
uspto-grants-2014_10
特許番号
US08859541B2

関連ノート

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