3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 71244902, compound

HRID 1397217Notes

Reaction equation

HRID 1397217 reaction equation
[C:1]1([C:7]2[CH: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:37])([F:36])[C:22]1[O:26][N:25]=[C:24]([C:27]2[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=2)[C:30](O)=[O:31])[N:23]=1>>[C:1]1([C:7]2[CH:8]=[C:9]([C:12]3([CH2:18][NH:19][C:30](=[O:31])[C:29]4[CH:33]=[CH:34][CH:35]=[C:27]([C:24]5[N:23]=[C:22]([C:21]([F:37])([F:36])[F:20])[O:26][N:25]=5)[CH:28]=4)[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 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67324343HCID 67324343, compound

Product 1

HCID 71244902HCID 71244902, compoundYield 20%

Procedure

This compound was synthesized from (4-(4-phenylthiophen-2-yl)tetrahydro-2H-pyran-4-yl)methanamine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (80 mg, yield 20%). 1H NMR (400 MHz, CDCl3) δ 8.43 (m, 1H), 8.25 (d, J=7.8 Hz, 1H), 7.96 (d, J=7.8 Hz, 1H), 7.62-7.58 (m, 3H), 7.45 (d, J=1.2 Hz, 1H), 7.40 (t, J=7.7 Hz, 2H), 7.31 (m, 1H), 7.23 (d, J=1.5 Hz, 1H), 6.15 (t, J=6.5 Hz, 1H), 3.96-3.91 (dt, J=11.9 Hz, 4.2 Hz, 2H), 3.74 (d, J=6.4 Hz, 2H), 3.71-3.66 (m, 2H), 2.18-2.14 (m, 2H), 2.08-2.03 (m, 2H). MS (ESI) m/z: Calculated for C26H22F3N3O3S: 513.13. found: 514.2 (M+H)+.

Sources & evidence

ORD record
ord-1ff1e2d793cf45759f77e15f8ab4e3f7
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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