Trifluoroacetic acid → Trifluoroacetic acid

HRID 416299Notes

Reaction equation

HRID 416299 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][C:15]2[S:19][C:18]([C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[NH:29]C(=O)OC(C)(C)C)=[O:21])=[CH:17][CH:16]=2)[N:8]=1.[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]>C(Cl)Cl>[NH2:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[NH:22][C:20]([C:18]1[S:19][C:15]([CH2:14][NH:13][C:9]2[N:8]=[C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH:12]=[CH:11][N:10]=2)=[CH:16][CH:17]=1)=[O:21].[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86614975HCID 86614975, compound

Product 2

HCID 6422Trifluoroacetic acidYield 75%HCID 66622549HCID 66622549, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 381 (35 mg, 0.07 mmol) in 1:1 mixture of DCM and TFA (4 mL) was stirred at room temperature for 30 minutes. The reaction mixture was concentrated to produce a solid which was triturated with ether to afford the title compound as a TFA salt (26 mg, 75% yield). 1H NMR (MeOH-d4) 9.31 (s, 1H), 8.68 (s, 1H), 8.66 (s, 1H), 8.43 (d, J=5.1 Hz, 1H), 7.77 (d, J=3.9 Hz, 1H), 7.68 (m, 1H), 7.1-7.5 (m, 6H). LRMS: (calc) 402.2; (found) 403.3 (M+H1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto produce a solid which
  3. customwas triturated with ether

Sources & evidence

ORD record
ord-2f09826d32134955badf1c66d720eeb9
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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