3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 69950060, compound

HRID 1397220Notes

Reaction equation

HRID 1397220 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]3([CH2:18][NH2:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[N: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[S:8][CH:9]=[C:10]([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)[N: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 67325071HCID 67325071, compound

Product 1

HCID 69950060HCID 69950060, compoundYield 45%

Procedure

This compound was synthesized from (4-(2-phenylthiazol-4-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 (85 mg, yield 45%). 1H NMR (400 MHz, DMSO-d6) δ 8.56 (t, J=6.2 Hz, 1H), 8.41 (m, 1H), 8.18 (d, J=7.8 Hz, 1H), 8.05 (d, J=7.6 Hz, 1H), 7.91-7.89 (m, 2H), 7.69-7.65 (t, J=7.8 Hz, 1H), 7.53 (s, 1H), 7.46-7.43 (dd, J=4.8 Hz, 1.9 Hz, 3H), 3.79-3.76 (m, 2H), 3.54-3.52 (d, J=6.2 Hz, 2H), 3.37 (m, 2H), 2.26-2.22 (d, J=13.8 Hz, 2H), 1.89-1.84 (m, 2H). MS (ESI) m/z: Calculated for C24H21F3N4O3S: 514.13. found: 515.0 (M+H)+.

Sources & evidence

ORD record
ord-1abffbcee37249b48e3c5739606067f9
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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