3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 67346279, compound

HRID 1397413Notes

Reaction equation

HRID 1397413 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH2:13][CH2:14][NH2:15])=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[F:16][C:17]([F:33])([F:32])[C:18]1[O:22][N:21]=[C:20]([C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=2)[C:26](O)=[O:27])[N:19]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]([CH2:13][CH2:14][NH:15][C:26](=[O:27])[C:25]3[CH:29]=[CH:30][CH:31]=[C:23]([C:20]4[N:19]=[C:18]([C:17]([F:33])([F:32])[F:16])[O:22][N:21]=4)[CH:24]=3)=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67324405HCID 67324405, compound

Product 1

HCID 67346279HCID 67346279, compoundYield 20%

Procedure

This compound was synthesized from 2-(2-(4-fluorophenyl)oxazol-5-yl)ethanamine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (28 mg, yield 20%). 1H NMR (400 MHz, MeOD) δ 8.56-8.55 (m, 1H), 8.30-8.28 (dq, J=7.8 Hz, 0.9 Hz, 1H), 8.06-8.04 (m, 1H), 8.00-7.96 (dd, J=9.0 Hz, 5.3 Hz, 2H), 7.71-7.69 (t, J=7.8 Hz, 1H), 7.21-7.17 (t, J=8.8 Hz, 2H), 7.03 (s, 1H), 3.78-3.75 (t, J=6.7 Hz, 2H), 3.15-3.12 (m, 2H). MS (ESI) m/z: Calculated for C21H14F4N4O3: 446.10. found: 447.0 (M+H)+.

Sources & evidence

ORD record
ord-63db074c1f714e27aa4c94b0a2de3458
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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