3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 71487697, compound

HRID 1397268Notes

Reaction equation

HRID 1397268 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:14]3([CH2:20][NH2:21])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[S:12][CH:13]=2)=[CH:5][CH:4]=1.[F:24][C:25]([F:41])([F:40])[C:26]1[O:30][N:29]=[C:28]([C:31]2[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=2)[C:34](O)=[O:35])[N:27]=1>>[F:40][C:25]([F:24])([F:41])[C:26]1[O:30][N:29]=[C:28]([C:31]2[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=2)[C:34]([NH:21][CH2:20][C:14]2([C:11]3[S:12][CH:13]=[C:9]([C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:22])[F:23])=[CH:8][CH:7]=4)[N:10]=3)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:35])[N:27]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67323794HCID 67323794, compound

Product 1

HCID 71487697HCID 71487697, compoundYield 19%

Procedure

This compound was synthesized from (4-(4-(4-(trifluoromethyl)phenyl)thiazol-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 (9 mgs, 19% yield). 1H NMR (300 MHz, CDCl3) δ 8.44 (s, 1H), 8.24 (d, J=7.7 Hz, 1H), 8.00 (m, 2H), 7.65-7.58 (m, 4H), 7.36 (s, 1H), 4.02-3.78 (m, 4H), 3.74 (m, 2H), 2.30 (m, 2H), 2.05 (m, 2H). MS (ESI) m/z: Calculated for C26H20F6N4O3S: 582.12. found: 583.1 (M+H)+.

Sources & evidence

ORD record
ord-3df1e22639d3459583eccfb5b469504b
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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