3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 71244911, compound

HRID 1397253Notes

Reaction equation

[NH2:1][CH2:2][C:3]1([C:9]2[S:10][CH:11]=[C:12]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[N:13]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]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>>[C:18]([C:17]1[CH:16]=[CH:15][C:14]([C:12]2[N:13]=[C:9]([C:3]3([CH2:2][NH:1][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)[CH2:4][CH2:5][O:6][CH2:7][CH2:8]3)[S:10][CH:11]=2)=[CH:21][CH:20]=1)#[N:19]

Participants

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid

HCID 67324111HCID 67324111, compound

Product 1

HCID 71244911HCID 71244911, compoundYield 7%

Procedure

This compound was synthesized from 4-(2-(4-(aminomethyl)tetrahydro-2H-pyran-4-yl)thiazol-4-yl)benzonitrile and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (3 mg, 7% yield). 1H NMR (300 MHz, CD3OD) δ 8.40 (d, J=1.8 Hz, 1H), 8.23 (d, J=7.2 Hz, 1H), 8.10-8.07 (m, 2H), 7.94 (m, 1H), 7.81 (m, 1H), 7.69-7.53 (m, 3H)) 3.94 (m, 2H), 3.87 (s, 2H), 3.55 (m, 2H), 2.45 (m, 2H), 2.08 (m, 2H). MS (ESI) m/z: Calculated for C26H20F3N5O3S: 539.12. found: 540.1 (M+H).

Sources & evidence

ORD record: ord-9a119f2c317f44f6a81a7ea4395931ea
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901156B2

Reaction notes

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