Trifluoroacetic acid → 4-[3-(4-Methyl-pyrimidin-5-yl)-benzenesulfonyl]-5-methylsulfanyl-thiophene-2-carboxamidine

HRID 2216192Notes

Reaction equation

HRID 2216192 reaction equation
C(OC(=O)[NH:7][C:8](=[NH:32])[C:9]1[S:10][C:11]([S:30][CH3:31])=[C:12]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[C:24]([CH3:29])=[N:25][CH:26]=[N:27][CH:28]=3)[CH:18]=2)(=[O:16])=[O:15])[CH:13]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.O>[CH3:29][C:24]1[C:23]([C:19]2[CH:18]=[C:17]([S:14]([C:12]3[CH:13]=[C:9]([C:8]([NH2:32])=[NH:7])[S:10][C:11]=3[S:30][CH3:31])(=[O:15])=[O:16])[CH:22]=[CH:21][CH:20]=2)=[CH:28][N:27]=[CH:26][N:25]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 145857624tert-butyl N-[4-[3-(4-methylpyrimidin-5-yl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 218866404-[3-(4-Methyl-pyrimidin-5-yl)-benzenesulfonyl]-5-methylsulfanyl-thiophene-2-carboxamidineYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent

Procedure

The (imino-{4-[3-(4-methyl-pyrimidin-5-yl)-benzenesulfonyl]-5-methylsulfanyl-thiophen-2-yl}-methyl)-carbamic acid tert-butyl ester ((Example 293: step a) 15 mg, 0.03 mmol) was dissolved in dichloromethane (1 mL), water (1 drop) was added, followed by trifluoroacetic acid (1 mL). The solution was stirred for 1 h 40 min at rt. The solvents were removed in vacuo, the residue was co-evaporated with dichloromethane and methanol, then purified by preparative TLC (10% methanol in dichloromethane) which yielded the title compound as a pale yellow glass (4 mg, 32%). 1H-NMR (CD3OD): δ 9.05 (s, 1H), 8.61 (s, 1H), 8.13–8.08 (m, 2H), 8.04 (s, 1H), 7.78–7.76 (m, 2H), 2.66 (s, 3H), 2.49 (s, 3H). ESI-MS (m/z): Calcd. for C17H16N4O2S3: 404.5 (M+H); found: 405.1.

Workup

  1. customThe solvents were removed in vacuo
  2. custompurified by preparative TLC (10% methanol in dichloromethane) which

Sources & evidence

ORD record
ord-73ba48c8e8124f7d8013ef68987cca31
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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