Trifluoroacetic acid → HCID 46184594, compound

HRID 387496Notes

Reaction equation

HRID 387496 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) δ 13.60 (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-e094f747a7f4471b85a643dc454b01f2
Source dataset
uspto-grants-2013_02
Patent number
US08372991B2

Reaction notes

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