N-bromobutanimide → (+/-)-cis-({3-[(5-Bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}oxy)acetic acid tert-butyl ester

HRID 2189038ノート

反応式

HRID 2189038 の反応式
[C:1]([O:5][C:6](=[O:31])[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([NH:15][C:16]2[C:17]3[CH:24]=[C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[O:22][C:18]=3[N:19]=[CH:20][N:21]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:39])C(=O)C1>ClC(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:31])[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([NH:15][C:16]2[C:17]3[C:24]([Br:39])=[C:23]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[O:22][C:18]=3[N:19]=[CH:20][N:21]=2)[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 86653749(+/-)-cis-({3-[(6-Phenylfuro[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}oxy)acetic acid tert-butyl ester

生成物 1

HCID 86653750(+/-)-cis-({3-[(5-Bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}oxy)acetic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

Suspend 132 mg (0.312 mmol) of (+/−)-cis-({3-[(6-phenylfuro[2,3-d]pyrimidin-4-yl)amino]cyclo-hexyl}oxy)acetic acid tert-butyl ester in 0.3 ml of tetrachloromethane, add 61 mg (0.343 mmol) of NBS and heat to reflux. On completion of conversion (approx. 1 h), cool the reaction mixture and isolate the product directly by preparative RP-HPLC. 104 mg (66.4% of theory) of the target compound are obtained.

後処理

  1. temperatureheat to reflux
  2. temperatureOn completion of conversion (approx. 1 h), cool the reaction mixture
  3. customisolate the product directly by preparative RP-HPLC
  4. custom104 mg (66.4% of theory) of the target compound are obtained

出典と根拠

ORDレコード
ord-c18aedb9675c43c6a8fe3d2523142e78
出典データセット
uspto-grants-2012_12
特許番号
US08324222B2

反応ノート

読み込み中…