5-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)thiophene-2-carboxylic acid → N-((4-(4-Phenyithiazol-2-yl)tetrahydro-2H-pyran-4-yl)methyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)thiophene-2-carboxamide

HRID 1397240Notes

Reaction equation

HRID 1397240 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:12]3([CH2:18][NH2:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:20][C:21]([F:36])([F:35])[C:22]1[O:26][N:25]=[C:24]([C:27]2[S:31][C:30]([C:32](O)=[O:33])=[CH:29][CH:28]=2)[N:23]=1>>[C:1]1([C:7]2[N:8]=[C:9]([C:12]3([CH2:18][NH:19][C:32]([C:30]4[S:31][C:27]([C:24]5[N:23]=[C:22]([C:21]([F:36])([F:20])[F:35])[O:26][N:25]=5)=[CH:28][CH:29]=4)=[O:33])[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 148719555-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)thiophene-2-carboxylic acidHCID 67322930(4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine

Product 1

HCID 69950125N-((4-(4-Phenyithiazol-2-yl)tetrahydro-2H-pyran-4-yl)methyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)thiophene-2-carboxamideYield 22%

Procedure

This compound was synthesized from (4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine and 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)thiophene-2-carboxylic acid as described in example 8 step 6 (25 mg, yield 22%): 1H NMR (400 MHz, CDCl3) δ 7.96 (d, J=7.3 Hz, 2H), 7.78 (m, J=4.0 Hz, 1H), 7.62 (br s, 1H), 7.53-7.48 (m, 4H), 7.42-7.38 (m, 1H), 3.97-3.91 (m, 2H), 3.86 (d, J=5.5 Hz, 2H), 3.78-3.73 (ddd, J=11.6 Hz, 7.5 Hz, 3.5 Hz, 2H), 2.33-2.27 (ddd, J=13.6 Hz, 7.0 Hz, 3.5 Hz, 2H), 2.06-1.99 (ddd, J=13.8 Hz, 7.3 Hz, 3.3 Hz, 2H). MS (ESI) m/z: Calculated for C23H19F3N4O3S2: 520.09. found: 521.0 (M+H)+.

Sources & evidence

ORD record
ord-efb6cb5706cc476793f5fd60cf8382d1
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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