3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 71280854, compound

HRID 1397266Notes

Reaction equation

HRID 1397266 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:14][NH2:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=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>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([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)[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 43345651HCID 43345651, compound

Product 1

HCID 71280854HCID 71280854, compoundYield 34%

Procedure

This compound was synthesized from (4-(3-bromophenyl)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 (40 mgs, 34% yield). 1H NMR (300 MHz, CDCl3) δ 8.30-8.22 (m, 2H) 7.86 (d, J=3.7 Hz, 1H), 7.60 (t, J=3.7 Hz, 1H), 7.52-7.44 (m, 2H), 7.38-7.30 (m, 2H), 3.90 (m, 2H), 3.71 (d, J=3.3 Hz, 2H), 3.64 (m, 2H), 2.13 (m, 2H), 2.02 (m, 2H). MS (ESI) m/z: Calculated for C22H19BrF3N3O3: 509.06. found: 509.9 (M+H)+.

Sources & evidence

ORD record
ord-80c860978ce04a00b7f4c5987e10d8a2
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

Loading…