N-bromobutanimide → 2-Propen-1-yl (3-{5-(2-chloro-4-pyrimidinyl)-2-[1-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-methylethyl]-1,3-thiazol-4-yl}-2-fluorophenyl)carbamate

HRID 239573ノート

反応式

HRID 239573 の反応式
BrN1C(=O)CCC1=O.[Cl:9][C:10]1[N:15]=[C:14]([CH2:16][C:17]([C:19]2[C:20]([F:32])=[C:21]([NH:25][C:26](=[O:31])[O:27][CH2:28][CH:29]=[CH2:30])[CH:22]=[CH:23][CH:24]=2)=O)[CH:13]=[CH:12][N:11]=1.[NH2:33][C:34](=[S:46])[C:35]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:37])[CH3:36]>ClCCl.CCOC(C)=O>[Cl:9][C:10]1[N:15]=[C:14]([C:16]2[S:46][C:34]([C:35]([NH:38][C:39]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:45])([CH3:37])[CH3:36])=[N:33][C:17]=2[C:19]2[C:20]([F:32])=[C:21]([NH:25][C:26](=[O:31])[O:27][CH2:28][CH:29]=[CH2:30])[CH:22]=[CH:23][CH:24]=2)[CH:13]=[CH:12][N:11]=1

参加物

6

反応物 3

HCID 67184N-bromobutanimideHCID 15186362tert-butyl N-(1-carbamothioyl-1-methylethyl)carbamateHCID 579899922-Propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}carbamate

生成物 1

HCID 579897572-Propen-1-yl (3-{5-(2-chloro-4-pyrimidinyl)-2-[1-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-methylethyl]-1,3-thiazol-4-yl}-2-fluorophenyl)carbamate収率 54.4%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

N-Bromosuccinimide (0.763 g, 4.29 mmol) was added to a solution of 2-propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}carbamate (1.5 g, 4.29 mmol) in dichloromethane (DCM) (50 mL). After 1 h of stirring, 1,1-dimethylethyl (2-amino-1,1-dimethyl-2-thioxoethyl)carbamate (0.936 g, 4.29 mmol) was added to the reaction mixture and heated to 80° C. for 2 h. The reaction mixture was diluted with 150 cc of EtOAc and washed with water (5×100 cc). The EtOAc layer was dried over MgSO4 and filtered and concentrated in vacuo. The residue was purified via chromatography on silica gel using Hex to 25% EtOAc in Hex to obtain the title compound (1.28 g, 54% yield). MS (ESI): 548.3 [M+H]+

後処理

  1. washwashed with water (5×100 cc)
  2. dry with materialThe EtOAc layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via chromatography on silica gel using Hex to 25% EtOAc in Hex

出典と根拠

ORDレコード
ord-5d2a4d96951b47849d69afeabe09bdc9
出典データセット
uspto-grants-2014_02
特許番号
US08642759B2

反応ノート

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