Sulfuric acid magnesium salt (1:1) → 2-[1-(Tert-butoxycarbonylamino-methyl)-6,7-dimethoxy-isoquinolin-4-ylamino]thiazole-4-carboxylic acid ethyl ester

HRID 14671

反応式

HRID 14671 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](=O)[C:31]([O:33][CH2:34][CH3:35])=[O:32].[O-]S([O-])(=O)=O.[Mg+2].[Al]>CC(C)=O>[CH2:34]([O:33][C:31]([C:30]1[N:26]=[C:24]([NH:23][C:12]2[C:13]3[C:18](=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=3)[C:9]([CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:27])=[N:10][CH:11]=2)[S:25][CH:29]=1)=[O:32])[CH3:35]

参加物

6

反応物 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 66144Ethyl bromopyruvateHCID 5359268AluminumHCID 59341094(6,7-Dimethoxy-4-thioureido-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester

生成物 1

HCID 593411022-[1-(Tert-butoxycarbonylamino-methyl)-6,7-dimethoxy-isoquinolin-4-ylamino]thiazole-4-carboxylic acid ethyl 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 ethyl bromopyruvate (30.4 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 g silica cartridge (MeOH/CH2Cl2, 1:99) to give 2-[1-(tert-butoxycarbonylamino-methyl)-6,7-dimethoxy-isoquinolin-4-ylamino]thiazole-4-carboxylic acid ethyl ester as a pale yellow solid (42.2 mg; 68%). 1H-NMR (CDCl3): δ, 8.51 (s, 1H), 7.48 (s, 1H), 7.42 (s, 1H), 6.13 (s, 1H), 4.91 (d, 2H, J=4.7 Hz), 4.39 (q, 2H, J=7.0 Hz), 4.05 (s, 3H), 3.99 (s, 3H), 1.50 (s, 9H), 1.40 (t, 3H, J=7.3 Hz); MS: calculated for C23H28N4O6S+H 489.0; found: 489.0.

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-67a86f5c9e7e48a680a0f66c18dac8ad
出典データセット
uspto-grants-2010_06
特許番号
US07732446B1

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