Ammonium Chloride → 4-[(3-Fluoro-4-methylphenyl)amino]-5-methylthiothiophene-2-carboxamidine

HRID 2186633Notes

Reaction equation

HRID 2186633 reaction equation
FC1C=C(N[C:10]2[CH:14]=[C:13]([S:15][CH3:16])[S:12][C:11]=2[C:17]([NH2:19])=[NH:18])C=CC=1C.[F:20][C:21]1[CH:22]=[C:23](NC2C=C(C(OC)=S)SC=2C)[CH:24]=[CH:25][C:26]=1[CH3:27].C[Al](C)C.[Cl-].[NH4+:44]>C1(C)C=CC=CC=1>[F:20][C:21]1[CH:22]=[C:23]([NH:44][C:14]2[CH:10]=[C:11]([C:17]([NH2:19])=[NH:18])[S:12][C:13]=2[S:15][CH3:16])[CH:24]=[CH:25][C:26]=1[CH3:27]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 86758186Methyl 4-[(3-fluoro-4-methylphenyl)amino]-5-methylthiothiophene-2-carboxylateHCID 136383542(3-Fluoro-4-methylphenyl)amino-5-methylthiothiophene-2-carboxamidine

Product 1

HCID 185371624-[(3-Fluoro-4-methylphenyl)amino]-5-methylthiothiophene-2-carboxamidineYield 44%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-[(3-Fluoro-4-methylphenyl)amino -5-methylthiothiophene-2-carboxamidine: The same procedure as in Example 253, step (b) was followed using 103 mg (0.349 mmol) of methyl 4-[(3-fluoro-4-methylphenyl)amino]-5-methylthiothiophene-2-carboxylate (as prepared in previous step), 2 mL of trimethylaluminum (2.0 M in toluene, 4 mmol), 216 mg of ammonium chloride (4 mmol) and 2 mL of toluene, and purified on a 2-g silica SPE column with 5% MeOH-CH2Cl2 to afford 45 mg (44%) of the title compound as a yellow foam 1H-NMR (DMSO-d6; 400 MHz) δ 2.13 (s, 3H), 2.50 (s, 3H ), 6.70 (m, 2H), 7.10 (m, 1H), 7.98 (s, 1H), 8.09 (s, 1H), 9.16 (br s, 4H). Mass spectrum (ESI, m/z): Calcd. for C13H14FN3S2, 296.1 (M+H), found 296.2.

Workup

  1. custompurified on a 2-g silica SPE column with 5% MeOH-CH2Cl2

Sources & evidence

ORD record
ord-01c05bdec75a4209aadab6c611cb771b
Source dataset
uspto-grants-2002_06
Patent number
US06403633B2

Reaction notes

Loading…