3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 53327948, compound

HRID 875027Notes

Reaction equation

HRID 875027 reaction equation
OC(C(F)(F)F)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[C:18]([CH2:20][N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[N:19]=2)=[CH:11][CH:10]=1.[F:27][C:28]([F:44])([F:43])[C:29]1[O:33][N:32]=[C:31]([C:34]2[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=2)[C:37](O)=[O:38])[N:30]=1>>[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[C:18]([CH2:20][N:21]3[CH2:22][CH2:23][N:24]([C:37]([C:36]4[CH:40]=[CH:41][CH:42]=[C:34]([C:31]5[N:30]=[C:29]([C:28]([F:43])([F:27])[F:44])[O:33][N:32]=5)[CH:35]=4)=[O:38])[CH2:25][CH2:26]3)[N:19]=2)=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 86673540HCID 86673540, compound

Product 1

HCID 53327948HCID 53327948, compoundYield 34%

Procedure

This compound was synthesized from 2-(4-fluorophenyl)-4-(piperazin-1-ylmethyl)thiazole TFA salt and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (26 mg, yield 34%). 1H NMR (400 MHz, CDCl3) δ 8.20-8.17 (m, 2H), 7.95-7.92 (dd, J=8.8 Hz, 5.1 Hz, 2H), 7.64-7.59 (m, 2H), 7.16-7.11 (m, 3H), 3.89 (m, 2H), 3.80 (s, 2H), 3.51 (m, 2H), 2.72 (m, 2H), 2.57 (m, 2H). MS (ESI) m/z: Calculated for C24H19F4N5O2S: 517.12. found: 518.2 (M+H)+

Sources & evidence

ORD record
ord-72d1a10e6d404ac182da6c2e888124f4
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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