3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 69950152, compound

HRID 1397222Notes

Reaction equation

HRID 1397222 reaction equation
[CH3:1][O:2][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:22][C:23]([F:39])([F:38])[C:24]1[O:28][N:27]=[C:26]([C:29]2[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=2)[C:32](O)=[O:33])[N:25]=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:14]3([CH2:20][NH:21][C:32](=[O:33])[C:31]4[CH:35]=[CH:36][CH:37]=[C:29]([C:26]5[N:25]=[C:24]([C:23]([F:39])([F:38])[F:22])[O:28][N:27]=5)[CH:30]=4)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[S:12][CH:13]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67325300HCID 67325300, compound

Product 1

HCID 69950152HCID 69950152, compoundYield 38%

Procedure

This compound was synthesized from (4-(4-(4-methoxyphenyl)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 (80 mg, yield 38%). 1H NMR (400 MHz, DMSO-d6) δ 8.78 (t, J=6.3 Hz, 1H), 8.43 (s, 1H), 8.20 (d, J=7.9 Hz, 1H), 8.07 (d, J=7.9 Hz, 1H), 7.91 (s, 1H), 7.86 (d, J=8.9 Hz, 2H), 7.71 (t, J=7.8 Hz, 1H), 6.95 (d, J=8.5 Hz, 2H), 3.86 (m, 2H), 3.77 (s, 3H), 3.58 (d, J=6.4 Hz, 2H), 3.43 (t, J=10.5 Hz, 2H), 3.33 (s, 2H), 2.25 (d, J=14 Hz, 2H), 2.02 (m, 2H). MS (ESI) m/z: Calculated for C26H23F3N4O4S: 544.14. found: 545.2 (M+H)+.

Sources & evidence

ORD record
ord-3ee48f9f4ee949819f3edfb3652b2aea
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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