1,2-Dichloroethane → 2-(Tetrahydro-pyran-2-yloxycarbamoyl)-benzo[b]thiophene-5-carboxylic acid methyl ester

HRID 545475ノート

反応式

HRID 545475 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[S:9][C:10]([C:12]([OH:14])=O)=[CH:11][C:7]=2[CH:6]=1)=[O:4].[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1NO.C(Cl)CCl.C1C=CC2[N:37]([OH:38])N=NC=2C=1.CCN(C(C)C)C(C)C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[S:9][C:10]([C:12](=[O:14])[NH:37][O:38][CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][O:17]3)=[CH:11][C:7]=2[CH:6]=1)=[O:4]

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13168123Tetrahydropyranyl hydroxylamineHCID 595564095-(Methoxycarbonyl)benzo[b]thiophene-2-carboxylic acid

生成物 1

HCID 589689592-(Tetrahydro-pyran-2-yloxycarbamoyl)-benzo[b]thiophene-5-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of benzo[b]thiophene-2,5-dicarboxylic acid 5-methyl ester (191.3 mg, 0.81 mmol), O -(Tetrahydro-pyran-2-yl)-hydroxylamine (93 mg, 0.79 mmol), EDC (231 mg, 1.20 mmol), HOBt (107 mg, 0.79 mmol) and DIEA (0.30 mL, 2.2 mmol) in anhydrous THF (8 mL) was allowed to stir at rt for three days and then concentrated. To the residue was added MeOH (1 mL) and water (10 mL) and Et2O (5 mL). After stirring for 2 h, the solid formed was washed with water (2×3 mL) and Et2O (5 mL), and dried to give 2-(tetrahydro-pyran-2-yloxycarbamoyl)-benzo[b]thiophene-5-carboxylic acid methyl ester as a pale solid). MS (EI): cal'd 252.0 (M−THP+H+), exp 252.1 (M−THP+H+).

後処理

  1. concentrationconcentrated
  2. additionTo the residue was added MeOH (1 mL) and water (10 mL) and Et2O (5 mL)
  3. stirringAfter stirring for 2 h
  4. customthe solid formed
  5. washwas washed with water (2×3 mL) and Et2O (5 mL)
  6. customdried

出典と根拠

ORDレコード
ord-6316083be0f54d14bc2a5da98ae2cce2
出典データセット
uspto-grants-2011_05
特許番号
US07935724B2

反応ノート

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