5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid → HCID 57606126, compound

HRID 1409847Notes

Reaction equation

HRID 1409847 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[O:7][N:6]=[C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=2)[C:4]=1[CH3:16].Cl.[F:20][C:21]([F:29])([F:28])[CH:22]1[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]1>>[CH3:16][C:4]1[C:5]([C:8]2[S:12][C:11]([C:13]([N:24]3[CH2:25][CH2:26][CH2:27][CH:22]([C:21]([F:29])([F:28])[F:20])[CH2:23]3)=[O:15])=[CH:10][CH:9]=2)=[N:6][O:7][C:3]=1[C:2]([F:1])([F:18])[F:17]

Participants

3

Reactant 2

HCID 252109975-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acidHCID 685664043-(Trifluoromethyl)piperidine hydrochloride

Product 1

HCID 57606126HCID 57606126, compound

Procedure

Prepared from 5-(5-Trifluoromethyl-4-methyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and (±)-3-trifluoromethylpiperidine hydrochloride by the method described in Example 41. Colorless solid (123 mg, 82%). 1H NMR (CDCl3) 1.53-1.76 (m, br, 2H), 1.84-1.95 (m, br, 1H), 2.10-2.22 (m, br, 1H), 2.31-2.43 (m, br, 4H), 2.92-3.16 (m, br, 2H), 4.28-4.45 (m, br, 1H), 4.54-4.72 (m, br, 1H), 7.34 (d, J=4.0, 1H), 7.47 (d, J=4.0, 1H). 13C NMR 7.7, 23.5, 24.2, 40.5 (q, J=27), 44.0 (br), 46.3 (br), 114.5 (q, J=2), 118.5 (q, J=271), 126.1 (q, J=283), 127.8, 129.1, 131.4, 139.3, 155.0 (q, J=41), 157.6, 162.8. 19F NMR −72.8, −63.2. LC/MS 6.99 min, [M+1]+ 413.

Workup

  1. customLC/MS 6.99 min, [M+1]+ 413

Sources & evidence

ORD record
ord-07b6959e71ab44c5ae816e5b52a5eee8
Source dataset
uspto-grants-2014_12
Patent number
US08921399B2

Reaction notes

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