5-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid → HCID 69950184, compound

HRID 1397355Notes

Reaction equation

HRID 1397355 reaction equation
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([CH2:13][NH2:14])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH:2]=1.[F:21][C:22]([F:38])([F:37])[C:23]1[O:27][N:26]=[C:25]([C:28]2[CH:29]=[N:30][CH:31]=[C:32]([CH:36]=2)[C:33](O)=[O:34])[N:24]=1>>[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([CH2:13][NH:14][C:33](=[O:34])[C:32]3[CH:36]=[C:28]([C:25]4[N:24]=[C:23]([C:22]([F:38])([F:37])[F:21])[O:27][N:26]=4)[CH:29]=[N:30][CH:31]=3)[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[CH:2]=1

Participants

3

Reactant 2

HCID 673242165-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acidHCID 67326010HCID 67326010, compound

Product 1

HCID 69950184HCID 69950184, compoundYield 48%

Procedure

This compound was synthesized from (4-([1,1′-biphenyl]-3-yl)tetrahydro-2H-pyran-4-yl)methanamine and 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid as described in example 8 step 6 (95 mg, yield 48%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 9.40 (br s, 1H), 8.97 (br s, 1H), 8.61-8.60 (t, J=1.9 Hz, 1H), 7.58-7.55 (m, 5H), 7.46-7.43 (t, J=7.5 Hz, 2H), 7.39-7.35 (m, 2H), 5.89-5.86 (t, J=6.1 Hz, 1H), 3.96-3.92 (m, 2H), 3.82-3.81 (d, J=6.1 Hz, 2H), 3.74-3.68 (m, 2H), 2.29-2.23 (m, 2H), 2.09-2.03 (m, 2H). MS (ESI) m/z: Calculated for C27H23F3N4O3: 508.17. found: 507.2 (M−H)−.

Sources & evidence

ORD record
ord-9e9696d88b0444bfab5ab5645c27cf7d
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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