Trifluoroacetic acid → HCID 22272828, compound

HRID 1064873Notes

Reaction equation

C([O:8][C:9]1[CH:41]=[CH:40][C:12]2[N:13]=[C:14]([S:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]([NH:28][C:29]4[C:30]([S:38][CH3:39])=[N:31][C:32]([CH3:37])=[CH:33][C:34]=4[S:35][CH3:36])=[O:27])[CH2:21][CH2:20]3)[NH:15][C:11]=2[CH:10]=1)C1C=CC=CC=1.FC(F)(F)C(O)=O>>[OH:8][C:9]1[CH:41]=[CH:40][C:12]2[N:13]=[C:14]([S:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]([NH:28][C:29]4[C:30]([S:38][CH3:39])=[N:31][C:32]([CH3:37])=[CH:33][C:34]=4[S:35][CH3:36])=[O:27])[CH2:21][CH2:20]3)[NH:15][C:11]=2[CH:10]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 11422109HCID 11422109, compound

Product 1

HCID 22272828HCID 22272828, compoundYield 76.5%

Procedure

2-[4-[2-(5-benzyloxybenzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide (115 mg, 0.189 mmol) obtained in Example 150 was dissolved into trifluoroacetic acid (2 ml) and stirred at room temperature for 23 hours. The reaction solution was concentrated in vacuo, and the resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:sat. ammonia methanol=10:1) to provide 75 mg (yield 76%) of the desired compound as colorless powdery crystals. IR (KBr) cm−1: 3227, 1675, 1600, 1564, 1486. 1H-NMR (CDCl3) δ: 2.36 (3H, s), 2.45 (3H, s), 2.47 (3H, s), 2.50-3.00 (10H, m), 3.10 (2H, s), 3.14 (2H, br s), 6.61 (1H, s), 6.74 (1H, d, J=8.8 Hz), 7.00 (1H, s), 7.29 (1H, d, J=8.8 Hz), 8.41 (1H, s).

Workup

concentrationThe reaction solution was concentrated in vacuo
customthe resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:sat. ammonia methanol=10:1)

Sources & evidence

ORD record: ord-36a9d1600bba455ea5efd7ab8e75d8eb
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969711B2

Reaction notes

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