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

HRID 1172849Notes

Reaction equation

HRID 1172849 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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+).

Workup

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

Sources & evidence

ORD record
ord-f7a81dc934d0475ba431e2e6d94f78de
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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