Trifluoroacetic acid → HCID 11960590, compound

HRID 1172862Notes

Reaction equation

HRID 1172862 reaction equation
[CH2:1]([O:8][C:9](=[O:38])[NH:10][CH2:11][C:12]1[CH:37]=[CH:36][C:15]2[CH:16]=[C:17]([C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[NH:28]C(OC(C)(C)C)=O)=[O:20])[S:18][C:14]=2[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:21][C:19]([C:17]1[S:18][C:14]2[CH:13]=[C:12]([CH2:11][NH:10][C:9](=[O:38])[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:37]=[CH:36][C:15]=2[CH:16]=1)=[O:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57624554HCID 57624554, compound

Product 1

HCID 11960590HCID 11960590, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl({2-[({2-[(tert-butoxycarbonyl)amino]phenyl}amino)carbonyl]-1-benzothien-6-yl}methyl)carbamate (85 mg, 0.16 mmol) in CH2Cl2 (4 mL) was added TFA (2 mL). The reaction mixture was stirred for 2 h, the solvent was removed. The residue was triturated with CH2Cl2 and sat. NaHCO3, and the resultant solid was filtered yielding the desired product. 1H NMR (DMSO-d6, 600 MHz) δ 10.05 (br s, 1H), 8.23 (s, 1H), 7.87 (m, 2H), 7.80 (s, 1H), 7.32-7.29 (m, 4H), 7.27 (m, 1H), 7.17 (br d, J=6.8 Hz, 1H), 7.02 (dd, J=6.8, 6.8 Hz, 1H), 6.87 (br d, J=6.8 Hz, 1H), 6.75 (br s, 1H), 5.00 (s, 2H), 4.29 (d, J=6.2 Hz, 2H). MS: cal'd 432 (MH+), exp 432 (MH+).

Workup

  1. customthe solvent was removed
  2. customThe residue was triturated with CH2Cl2 and sat. NaHCO3
  3. filtrationthe resultant solid was filtered

Sources & evidence

ORD record
ord-b57fe66b04004de39f3b50452ec0697b
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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