Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylate → HCID 16718793, compound

HRID 1916347Notes

Reaction equation

HRID 1916347 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([O:15]C)=O)=[C:10]([N:17]=[CH:18][N:19]([CH3:21])C)[CH:9]=2)=[CH:4][CH:3]=1.NC1[CH:37]=[CH:36][C:26]([O:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[C:25]([O:38][CH3:39])[CH:24]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]3[C:13](=[O:15])[N:19]([C:21]4[CH:37]=[CH:36][C:26]([O:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])=[C:25]([O:38][CH3:39])[CH:24]=4)[CH:18]=[N:17][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 11544322Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylateHCID 58858064HCID 58858064, compound

Product 1

HCID 16718793HCID 16718793, compoundYield 34%

Procedure

Condensation of methyl 5-(4-chlorophenyl)-3-((dimethylamino)methylene-amino)-thiophene-2-carboxylate (740 mg) and tert-butyl 2-(4-amino-2-methoxy-phenoxy)acetate Part C (581 mg) as described in Example 1 yielded the title compound 388 mg (34%). 1H NMR (CDCl3) δ 1.50 (s, 9H), 3.92 (s, 3H), 4.65 (s, 2H), 6.91 (br s, 2H), 6.99 (br s, 1H), 7.44 (d, J=8.24 Hz, 2H), 7.53 (s, 1H), 7.65 (d, J=8.25 Hz, 2H), 8.14 (s, 1H); 13C NMR (CDCl3) δ 28.04, 56.21, 66.57, 82.58, 111.28, 113.76, 118.98, 120.86, 123.21, 127.65, 129.45, 130.85, 131.52, 135.68, 148.12, 150.00, 151.66, 156.73, 157.36, 167.51; HPLC (Method #1): 3.89 min retention time; MS (ES): m/z 499 [M+H]+.

Sources & evidence

ORD record
ord-869dfce7ba7f4778b07ee4d597252ab3
Source dataset
uspto-grants-2013_12
Patent number
US08618115B2

Reaction notes

Loading…