Diisopropylethylamine → 2-Amino-6-(4-methoxy-benzyl)-5-(6-methoxy-4-methoxycarbonyl-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester

HRID 1242116ノート

反応式

HRID 1242116 の反応式
[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH:14]([CH2:17][NH2:18])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[CH2:12][C:11]=2[S:10][C:9]=1[NH2:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.C[O:39][C:40](=O)[C:41]1[CH:50]=[C:49]([O:51][CH3:52])[CH:48]=[C:43]([C:44]([O:46][CH3:47])=[O:45])[C:42]=1[CH2:53]Br>C(#N)C>[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH:14]([CH2:17][N:18]3[CH2:53][C:42]4[C:41](=[CH:50][C:49]([O:51][CH3:52])=[CH:48][C:43]=4[C:44]([O:46][CH3:47])=[O:45])[C:40]3=[O:39])[N:13]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[CH2:12][C:11]=2[S:10][C:9]=1[NH2:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 40709542-Bromomethyl-5-methoxy-isophthalic acid dimethyl esterHCID 695855102-Amino-5-aminomethyl-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester

生成物 1

HCID 695856332-Amino-6-(4-methoxy-benzyl)-5-(6-methoxy-4-methoxycarbonyl-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester収率 71.8%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 2-amino-5-aminomethyl-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (57.4 mg, 0.142 mmol) and diisopropyl ethylamine (49 μl, 0.28 mmol) in acetonitrile (20 ml) at room temperature was added 2-bromomethyl-5-methoxy-isophthalic acid dimethyl ester (3.00 g, 7.45 mmol). The solution was stirred for 16 hours and the solvent evaporated in vacuo. The residue was taken into ethyl acetate (50 ml) and washed with water (2×20 ml), 1 N hydrochloric acid (20 ml), brine, dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was chromatographed on silica gel column using a mixture of ethyl acetate/hexane (1:1) as eluent, which afforded 62 mg (71%) of 2-amino-6-(4-methoxy-benzyl)-5-(6-methoxy-4-methoxycarbonyl-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as a solid.

後処理

  1. customthe solvent evaporated in vacuo
  2. washwashed with water (2×20 ml), 1 N hydrochloric acid (20 ml), brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customThe residue was chromatographed on silica gel column
  7. additiona mixture of ethyl acetate/hexane (1:1) as eluent

出典と根拠

ORDレコード
ord-276645f8f9454f2bbc3a96a1fd6fc76c
出典データセット
uspto-grants-2006_10
特許番号
US07115624B1

反応ノート

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