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

HRID 545475노트

반응식

HRID 545475 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-6316083be0f54d14bc2a5da98ae2cce2
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935724B2

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