Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylate → HCID 86618696, compound

HRID 2239373Notes

Reaction equation

HRID 2239373 reaction equation
[NH2:1][CH2:2][C:3]1[N:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=1.C[O:24][C:25]([C:27]1[S:28][C:29]([C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)=[CH:30][C:31]=1[N:32]=[CH:33]N(C)C)=O>>[Cl:43][C:40]1[CH:39]=[CH:38][C:37]([C:29]2[S:28][C:27]3[C:25](=[O:24])[N:1]([CH2:2][C:3]4[N:8]=[C:7]([O:9][CH:10]5[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]5)[CH:6]=[CH:5][CH:4]=4)[CH:33]=[N:32][C:31]=3[CH:30]=2)=[CH:42][CH:41]=1

Participants

3

Reactant 2

HCID 11544322Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylateHCID 68713655HCID 68713655, compound

Product 1

HCID 86618696HCID 86618696, compound

Procedure

Prepared from tert-butyl 4-{[6-(aminomethyl)pyridin-2-yl]oxy}piperidine-1-carboxylate (629 mg, 2.05 mmol) and 5-(4-chloro-phenyl)-3-(dimethylamino-methyleneamino)-thiophene-2-carboxylic acid methyl ester (662 mg, 2.05 mmol) according to the procedure in Example 14c. Purification by silica gel flash chromatography using a 40+M Biotage column with a gradient of 10-100% EtOAc in heptane yielded the title compound as a colorless solid. Yield: 679 mg (60%). 1H NMR (400 MHz, CDCl3) δ 8.27 (s, 1H), 7.60 (m, 2H), 7.53 (t, 1H, J=7.7 Hz), 7.46 (s, 1H), 7.39 (m, 2H), 6.95 (d, 1H, J=7.2 Hz), 6.60 (d, 1H, J=8.2 Hz), 5.18 (s, 2H), 4.96 (m, 1H), 3.66 (m, 2H), 3.09 (m, 2H), 1.78 (m, 2H), 1.56 (m, 2H), 1.41 (s, 9H).

Workup

  1. customPurification by silica gel flash chromatography

Sources & evidence

ORD record
ord-ebba0104465e4239b8ad63624e24be30
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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