Trifluoroacetic acid → HCID 69026655, compound

HRID 1433038Notes

Reaction equation

HRID 1433038 reaction equation
C(OC([N:8]1[C:12]([CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[S:29][C:28]4[CH:30]=[C:31]([Cl:34])[CH:32]=[CH:33][C:27]=4[CH:26]=3)(=[O:24])=[O:23])[CH2:18][C:17]2=[O:35])=[CH:11][N:10]=[CH:9]1)=O)(C)(C)C.[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>C(Cl)Cl>[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[Cl:34][C:31]1[CH:32]=[CH:33][C:27]2[CH:26]=[C:25]([S:22]([N:19]3[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][CH2:13][C:12]4[NH:8][CH:9]=[N:10][CH:11]=4)[C:17](=[O:35])[CH2:18]3)(=[O:24])=[O:23])[S:29][C:28]=2[CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57311386HCID 57311386, compound

Product 1

HCID 69026655HCID 69026655, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-{3-[4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-yl]-propyl}-imidazol-1carboxylic acid tert-butyl ester (30 mg, 0.055 mmol) is stirred vigorously in a 30% solution of trifluoroacetic acid and methylene chloride (2 mL). The reaction is complete after stirring for three hours. The volatile solvents are removed on the rotovap, and the gummy solid is titurated with ether several times to afford 4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-1-[3-(3H-imidazol-4-yl)-propyl]-piperazin-2-one trifluoroacetic acid salt (30 mg) as a yellow solid. C18H19ClN4O3S2 (m/z)+: 439, 441. Anal cald. for C18H19ClN4O3S2.C2HF3O2: C, 43.44; H, 3.65; N, 10.13. Found C, 42.03; H, 3.55; N, 8.26.

Workup

  1. customThe volatile solvents are removed on the rotovap

Sources & evidence

ORD record
ord-706aaf9e0a0940deb2c9d881a7ce62f2
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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