Trifluoroacetic acid → HCID 46186149, compound

HRID 387499Notes

Reaction equation

HRID 387499 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]([CH:37]([F:39])[F:38])[C:35]3[CH:40]=[CH:41][CH:42]=[CH:43][C:34]=3[N: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]([CH:37]([F:38])[F:39])[C:35]3[CH:40]=[CH:41][CH:42]=[CH:43][C:34]=3[N:33]=2)[C:24]=1[C:25]([OH:27])=[O:26])=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67308249HCID 67308249, compound

Product 1

HCID 46186149HCID 46186149, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of argon, trifluoroacetic acid (0.75 mL) was added to a stirred solution of 43 (33 mg, 65 μmol) in dichloromethane (0.75 mL) at room temperature. The reaction was stirred for 6 hours then concentrated under reduced pressure. Flash chromatography (silica, 5% methanol in dichloromethane) provided 44 (26.2 mg, 90%) as a solid: 1H NMR (500 MHz, d6-DMSO) δ 13.70 (bs, 1H), 12.46 (s, 1H), 7.92 (s, 1H), 7.88 (d, J=7.9 Hz, 1H), 7.81-7.72, (m, 3H), 7.65-7.54 (m, 2H), 7.44-7.38 (m, 4H); LRESIMS m/z 454 [M+H]+, calcd. for C22H13F2N3O4S1 454.1.

Workup

  1. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-1e1af55e5114438aa4f8014148d48861
Source dataset
uspto-grants-2013_02
Patent number
US08372991B2

Reaction notes

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