3-[5-(Trifluoroacetyl)thiophen-2-yl]benzoic Acid → N-((4-(2-(4-Chlorophenyl)thiazol-4-yl)-1-methylpiperidin-4-yl)methyl)-3-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)benzamide

HRID 1397383Notes

Reaction equation

HRID 1397383 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]3([CH2:20][NH2:21])[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)[N:12]=2)=[CH:4][CH:3]=1.[F:22][C:23]([F:41])([F:40])[C:24]([C:26]1[S:30][C:29]([C:31]2[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=2)[C:34](O)=[O:35])=[CH:28][CH:27]=1)=[O:25]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]3([CH2:20][NH:21][C:34](=[O:35])[C:33]4[CH:37]=[CH:38][CH:39]=[C:31]([C:29]5[S:30][C:26]([C:24](=[O:25])[C:23]([F:22])([F:40])[F:41])=[CH:27][CH:28]=5)[CH:32]=4)[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]3)[N:12]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 248966243-[5-(Trifluoroacetyl)thiophen-2-yl]benzoic AcidHCID 67323091(4-(2-(4-Chlorophenyl)thiazol-4-yl)-1-methylpiperidin-4-yl)methanamine

Product 1

HCID 67325581N-((4-(2-(4-Chlorophenyl)thiazol-4-yl)-1-methylpiperidin-4-yl)methyl)-3-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)benzamideYield 4%

Procedure

This compound was synthesized from (4-(2-(4-chlorophenyl)thiazol-4-yl)-1-methylpiperidin-4-yl)methanamine and 3-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)benzoic acid as described in example 8 step 6 (8.5 mg, yield 4%). 1H NMR (400 MHz, DMSO-d6) δ 8.54 (m, 1H), 8.14-8.13 (m, 2H), 8.00-7.86 (m, 4H), 7.82-7.77 (m, 1H), 7.70 (m, 1H), 7.60-7.56 (m, 1H), 7.48-7.46 (m, 2H), 3.50 (m, 2H), 3.39-3.17 (m, 4H), 2.57 (m, 3H), 2.43 (m, 2H), 2.08 (m, 2H).

Sources & evidence

ORD record
ord-cb8f0083225b47abb461dee3e291a263
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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