3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 69950068, compound

HRID 1397233Notes

Reaction equation

HRID 1397233 reaction equation
[CH: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)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]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>>[CH:1]1([C:7]2[N: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)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67324815HCID 67324815, compound

Product 1

HCID 69950068HCID 69950068, compoundYield 32%

Procedure

This compound was synthesized from (4-(4-cyclohexylthiazol-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 (70 mg, yield 32%). 1H NMR (400 MHz, MeOD) δ 8.50 (t, J=1.5 Hz, 1H), 8.29 (dt, J=7.8 Hz, 1.4 Hz, 1H), 7.98 (m, 1H), 7.67 (t, J=7.8 Hz, 1H), 7.05 (s, 1H), 3.90-3.86 (dt, J=11.8 Hz, 3.9 Hz, 2H), 3.65 (s, 2H), 3.55-3.49 (m, 2H), 2.69 (m, 1H), 2.35 (d, J=13.8 Hz, 2H), 2.04-1.96 (m, 4H), 1.76-1.73 (m, 2H), 1.39 (m, 6H). MS (ESI) m/z: Calculated for C25H27F3N4O3S: 520.18. found: 521.2 (M+H)+.

Sources & evidence

ORD record
ord-8a781627c67f4ee18d44abe000ad19e6
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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