Phenacyl bromide → [6,7-Dimethoxy-4-(4-phenyl-thiazol-2-ylamino)isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester

HRID 14667

反応式

HRID 14667 の反応式
[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[C:12]([NH:23][C:24]([NH2:26])=[S:25])=[CH:11][N:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=O.[O-]S([O-])(=O)=O.[Mg+2].[Al]>CC(C)=O>[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[C:12]([NH:23][C:24]2[S:25][CH:29]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:26]=2)=[CH:11][N:10]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 6259Phenacyl bromideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5359268AluminumHCID 59341094(6,7-Dimethoxy-4-thioureido-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester

生成物 1

HCID 59341076[6,7-Dimethoxy-4-(4-phenyl-thiazol-2-ylamino)isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A solution of (6,7-dimethoxy-4-thioureido-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester (50 mg, 0.127 mmol) and 2-bromoacetophenone (27.9 mg, 0.140 mmol) in acetone (1.4 mL) in a conical vial was added MgSO4 (7.7 mg, 0.0637 mmol). The resulting suspension was placed in an aluminum block preheated to 60° C. and was allowed to stir for 3.0 h. The reaction was cooled and concentrated. The residue was purified using a 5.0 g silica cartridge (MeOH/CH2Cl2, 1:99) to give [6,7-dimethoxy-4-(4-phenyl-thiazol-2-ylamino)isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester as a yellow solid (44.6 mg; 71%). 1H-NMR (CDCl3): δ, 8.64 (s, 1H), 7.52-7.41 (m, 6H), 6.76 (s, 1H), 6.17 (s, 1H), 4.92 (d, 2H, J=4.7 Hz), 4.06 (s, 3H), 4.02 (s, 3H), 1.51 (s, 9H); MS: calculated for C26H28N4O4S+H 493.5; found: 493.5.

後処理

  1. custompreheated to 60° C.
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. customThe residue was purified

出典と根拠

ORDレコード
ord-88568eeb7f734799adab4c78c72699f8
出典データセット
uspto-grants-2010_06
特許番号
US07732446B1

関連ノート

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