tert-butyl N-[5-methylsulfanyl-4-[3-[5-methyl-1-(2-trimethylsilylethoxymethyl)benzimidazol-4-yl]phenyl]sulfonylthiophene-2-carboximidoyl]carbamate → 4-[3-(5-Methyl-1H-benzoimidazol-4-yl)-benzenesulfonyl]-5-methylsulfanyl-thiophene-2-carboxamidine

HRID 723238Notes

Reaction equation

HRID 723238 reaction equation
C(OC(=O)[NH:7][C:8](=[NH:43])[C:9]1[S:10][C:11]([S:41][CH3:42])=[C:12]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[C:31]4[N:30]=[CH:29][N:28](COCC[Si](C)(C)C)[C:27]=4[CH:26]=[CH:25][C:24]=3[CH3:40])[CH:18]=2)(=[O:16])=[O:15])[CH:13]=1)(C)(C)C>C(O)(C(F)(F)F)=O>[CH3:40][C:24]1[CH:25]=[CH:26][C:27]2[NH:28][CH:29]=[N:30][C:31]=2[C:23]=1[C:19]1[CH:18]=[C:17]([S:14]([C:12]2[CH:13]=[C:9]([C:8]([NH2:43])=[NH:7])[S:10][C:11]=2[S:41][CH3:42])(=[O:15])=[O:16])[CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 1

HCID 145857650tert-butyl N-[5-methylsulfanyl-4-[3-[5-methyl-1-(2-trimethylsilylethoxymethyl)benzimidazol-4-yl]phenyl]sulfonylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 218867264-[3-(5-Methyl-1H-benzoimidazol-4-yl)-benzenesulfonyl]-5-methylsulfanyl-thiophene-2-carboxamidineYield 150.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of [Imino-(5-methylsulfanyl-4-{3-[5-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-4-yl]-benzenesulfonyl}-thiophen-2-yl)-methyl]-carbamic acid tert-butyl ester (14 mg, 0.021 mmol, Example 287: step c) in 1 mL of TFA was heated at 50° C. for 2 h under Ar, cooled to RT. Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (10–15% MeOH/CH2Cl2) gave 14 mg (100%) of product as colorless oil: 1H-NMR (CD3OD; 400 MHz) δ 9.28 (s, 1H). 8.35 (s, 1H), 8.20 (d, 1H, J=7.6 Hz). 8.11 (s, 1H), 7.86 (dd, 1H, J=7.7, 7.7), 7.80 (m, 2H), 7.63 (d, 1H, J=8.6 Hz), 2.72 (s, 3H), 2.30 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C20H18N4O2S3, 443.1.00 (M+H), found 443.1.

Workup

  1. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-36c3ad58bc9e4749978ee07f8d17d46a
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

Loading…