Methanol → Methyl 4-(4-{4-[(toluenesulfonyl)amino]phenyl}(1,3-thiazol-2-yl))-5-methylthiothiophene-2-carboxylate

HRID 2298622Notes

Reaction equation

HRID 2298622 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]3[CH:14]=[C:15]([C:19]([O:21][CH3:22])=[S:20])[S:16][C:17]=3[CH3:18])[S:11][CH:12]=2)=[CH:4][CH:3]=1.CN1[CH2:29][CH2:28]OCC1.[C:30]1(C)[CH:35]=C[C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1.CO>ClCCl>[C:28]1([CH3:29])[C:33]([S:36]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:9]=[C:10]([C:13]4[CH:14]=[C:15]([C:19]([O:21][CH3:22])=[S:20])[S:16][C:17]=4[CH3:18])[S:11][CH:12]=3)=[CH:4][CH:3]=2)(=[O:38])=[O:37])=[CH:32][CH:31]=[CH:30][CH:35]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 73974-Toluenesulfonyl chlorideHCID 79724-MethylmorpholineHCID 86583820Methyl 4-(4-(4-aminophenyl)(1,3-thiazol-2-yl))-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86758675Methyl 4-(4-{4-[(toluenesulfonyl)amino]phenyl}(1,3-thiazol-2-yl))-5-methylthiothiophene-2-carboxylateYield 44.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 4-(4-(4-aminophenyl)(1,3-thiazol-2-yl))-5-methylthiothiophene-2-carboxylate (33 mg, 0.09 mmol) was dissolved in dry dichloromethane (5 mL). To this, N-methyl morpholine (10 μL, 0.09 mmol) and p-toluenesulfonyl chloride (17 mg, 0.09 mmol) was added and the mixture was stirred at room temperature for 5 days. Workup was carried out as in Example 134, step (c). Trituration with dichloromethane and methanol gave methyl 4-(4-{4-[(toluenesulfonyl)amino]phenyl}(1,3-thiazol-2-yl))-5-methylthiothiophene-2-carboxylate (20 mg, 43%) as a brown solid. 1H-NMR (DMSO-d6; 300 MHz) δ10.39 (s, 1H), 8.19 (s, 1H), 8.05 (s, 1H), 7.91 and 7.18 (AB quartet, 2H, J=8.7 Hz), 7.68 and 7.35 (AB quartet, 2H, J=8.2 Hz), 3.85 (s, 3H), 2.74 (s, 3H), 2.27 (s, 3H). Mass spectrum (MALDI-TOF, CHCA matrix, m/z): Calcd. for C23H20N2O4S4, 517.2 (M+H), found 517.0.

Sources & evidence

ORD record
ord-e8cde15c57684632b9068cec0866e582
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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