Trifluoroacetic acid → HCID 71467867, compound

HRID 535533Notes

Reaction equation

HRID 535533 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18](=[O:25])[N:17]([NH:26][C:27](=[O:36])[CH2:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[N:16]=2)=[CH:10][CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[CH:9]=[CH:10][C:11]([S:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18](=[O:25])[N:17]([NH:26][C:27](=[O:36])[CH2:28][C:29]3[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=3)[N:16]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131731941HCID 131731941, compound

Product 1

HCID 71467867HCID 71467867, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 103C (23 mg, 0.043 mmol) in CH2Cl2 (4 mL) was treated with TFA (1 mL). The reaction mixture was stirred at room temperature for 20 minutes, concentrated, and the resulting residue was purified by HPLC (conditions from Example 10C) to afford 9.3 mg (50%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.56 (s, 1H), 8.31 (dd, J=7.9, 0.9, 1H), 8.12 (d, J=7.8, 1H), 8.06-7.98 (m, 1H), 7.97-7.89 (m, 1H), 7.46-7.36 (m, 2H), 7.34-7.28 (m, 2H), 7.24-7.15 (m, 2H), 6.64-6.56 (m, 2H), 3.63 (s, 2H); MS (APCI+) M/Z 437 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customthe resulting residue was purified by HPLC (conditions from Example 10C)

Sources & evidence

ORD record
ord-d08a517d25084283bf2e9ade0e4b0bce
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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