Trifluoroacetic acid → HCID 46184594, compound

HRID 1013551Notes

Reaction equation

HRID 1013551 reaction equation
FC(F)(F)C(O)=O.[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH:10]=[C:9]1[C:17]([NH:19][C:20]1[S:21][CH:22]=[C:23]([C:32]2[N:36]([CH3:37])[N:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=2)[C:24]=1[C:25]([O:27]C(C)(C)C)=[O:26])=[O:18]>ClCCl>[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH:10]=[C:9]1[C:17]([NH:19][C:20]1[S:21][CH:22]=[C:23]([C:32]2[N:36]([CH3:37])[N:35]=[C:34]([C:38]([F:39])([F:40])[F:41])[CH:33]=2)[C:24]=1[C:25]([OH:27])=[O:26])=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59225732HCID 59225732, compound

Product 1

HCID 46184594HCID 46184594, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of argon, trifluoroacetic acid (1.0 mL) was added to a stirred solution of 13 (21 mg, 43 μmol) in dichloromethane (1.0 mL) at room temperature. The reaction was stirred for 45 minutes then concentrated under reduced pressure. The material was washed with dichloromethane to provided 14 (3.4 mg, 18%) as a solid: 1H NMR (500 MHz, d6-DMSO) 513.60 (bs, 1H), 12.55 (bs, 1H), 7.87 (m, 2H), 7.76 (dd, J=8.4, 1.3 Hz, 1H), 7.58 (ddd, J=7.8, 7.8, 1.2 Hz, 1H), 7.42 (ddd, J=7.7, 7.7, 0.7 Hz, 1H), 7.34, (s, 1H), 6.76 (s, 1H), 6.37 (s, 3H); LRESIMS m/z 436 [M+H]+, calcd. for C19H12F3N3O4S1 436.1.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. washThe material was washed with dichloromethane

Sources & evidence

ORD record
ord-e417d7f0264d4bdba029a3caa88cc9a3
Source dataset
uspto-grants-2011_07
Patent number
US07981925B2

Reaction notes

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