3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 69950094, compound

HRID 1397219Notes

Reaction equation

HRID 1397219 reaction equation
[C:1]1([C:7]2[N:11]=[C:10]([C:12]3([CH2:18][NH2:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[NH:9][N:8]=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[N:11]=[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)[NH:9][N:8]=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 67325177HCID 67325177, compound

Product 1

HCID 69950094HCID 69950094, compoundYield 24%

Procedure

This compound was synthesized from (4-(3-phenyl-1H-1,2,4-triazol-5-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 24%). 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 1H), 8.25 (d, J=7.8 Hz, 1H), 8.11 (d, J=7.8 Hz, 1H), 8.02 (dd, J=7.3 Hz, 1.8 Hz, 2H), 7.89 (br s, 1H), 7.62 (t, J=7.8 Hz, 1H), 7.46 (m, 3H), 3.97-3.92 (dt, J=11.9 Hz, 4.5 Hz, 2H), 3.83 (d, J=5.8 Hz, 2H), 3.71-3.66 (m, 2H), 2.44-2.42 (d, J=13.6 Hz, 2H), 1.96-1.89 (ddd, J=13.4 Hz, 9.2 Hz, 3.5 Hz, 2H). MS (ESI) m/z: Calculated for C24H21F3N6O3: 498.16. found: 499.2 (M+H)+.

Sources & evidence

ORD record
ord-ecae48f7728247478b75bceed979ef3f
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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