Trifluoroacetic acid → HCID 46890683, compound

HRID 1013166Notes

Reaction equation

HRID 1013166 reaction equation
C([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[S:19](=[O:27])(=[O:26])[NH:18]2)=[CH:9]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[O:27]=[S:19]1(=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH:17]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:8]([CH2:7][C:6]([OH:28])=[O:5])[CH:9]=2)[NH:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 67316103HCID 67316103, compound

Product 1

HCID 46890683HCID 46890683, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of example 1, step d (32 mg, 0.08 mmol) was treated with trifluoroacetic acid (TFA) (neat) or 70% TFA in DCM. After stirring 2-24 h, the reaction was concentrated to dryness and purified by preparative LCMS to give the title compound. 1H NMR (DMSO-d6) δ 7.90-7.86 (m, 1H), 7.66-7.57 (m, 2H), 7.38 (s, 1H), 7.29 (d, J=8.1 Hz, 1H), 7.25-7.20 (m, 2H), 7.06 (t, J=7.2 Hz, 1H), 6.87 (t, J=7.2 Hz, 1H), 6.07 (s, 1H), 4.62 (s, 2H); MS: ESI (negative): 341 (M−H).

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-adff59b9155642db876f3862274bacc8
Source dataset
uspto-grants-2011_07
Patent number
US07981912B2

Reaction notes

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