O-Phenylenediamine → Methyl 2-{[(2-aminophenyl)amino]carbonyl}-1-benzothiophene-6-carboxylate

HRID 1172849노트

반응식

HRID 1172849 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH:12]=[C:11]([C:13]([OH:15])=O)[S:10][C:9]=2[CH:16]=1)=[O:4].CCN=C=NCCCN(C)C.[CH:28]1[CH:29]=[CH:30][C:31]2[N:36](O)N=[N:34][C:32]=2[CH:33]=1.C1(N)C=CC=CC=1N>CN(C=O)C>[NH2:34][C:32]1[CH:33]=[CH:28][CH:29]=[CH:30][C:31]=1[NH:36][C:13]([C:11]1[S:10][C:9]2[CH:16]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=[CH:7][C:8]=2[CH:12]=1)=[O:15]

참가 물질

6

반응물 4

HCID 7243O-PhenylenediamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 595564196-(Methoxycarbonyl)benzo[b]thiophene-2-carboxylic acid

생성물 1

HCID 57624546Methyl 2-{[(2-aminophenyl)amino]carbonyl}-1-benzothiophene-6-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of benzo[b]thiophene-2,6-dicarboxylic acid 6-methyl ester (129 mg, 0.543 mmol) in DMF (4 mL) was added EDCI (125 mg, 0.652 mmol), HOBt (88 mg, 0.652 mmol). The reaction mixture was stirred for 20 min and phenylene diamine (147 mg, 1.36 mmol) was added. After 18 h, the solvent was removed and EtOAc and H2O were added. The resultant solid was filtered yielding the desired product. 1H NMR (CDCl3, 600 MHz) δ 8.53 (s, 1H), 8.01 (s, 1H), 7.99 (d, J=7.9 Hz, 1H), 7.86 (d, J=7.9 Hz, 1H), 7.23 (d, J=6.8 Hz, 1H), 7.05 (t, J=6.8 Hz, 1H), 6.81 (d, J=6.8 Hz, 1H), 6.80 (t, J=6.8 Hz, 1H), 3.90 (s, 3H). MS: cal'd 327 (MH+), exp 327 (MH+).

후처리

  1. waitAfter 18 h
  2. customthe solvent was removed
  3. additionEtOAc and H2O were added
  4. filtrationThe resultant solid was filtered

출처 및 근거

ORD 기록
ord-f7a81dc934d0475ba431e2e6d94f78de
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834034B2

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