Isobutylamine → 2-{[2-fluoro-6-(trifluoromethyl)benzoyl]amino}-N-isobutyl-4,4,6,6-tetramethyl-4,6-dihydrothieno[2,3-c]furan-3-carboxamide

HRID 1015599Notes

Reaction equation

HRID 1015599 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[C:3]=1[C:4]([NH:6][C:7]1[S:18][C:10]2[C:11]([CH3:17])([CH3:16])[O:12][C:13]([CH3:15])([CH3:14])[C:9]=2[C:8]=1[C:19](O)=[O:20])=[O:5].[CH2:30]([NH2:34])[CH:31]([CH3:33])[CH3:32]>>[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[C:3]=1[C:4]([NH:6][C:7]1[S:18][C:10]2[C:11]([CH3:16])([CH3:17])[O:12][C:13]([CH3:15])([CH3:14])[C:9]=2[C:8]=1[C:19]([NH:34][CH2:30][CH:31]([CH3:33])[CH3:32])=[O:20])=[O:5]

Participants

3

Reactant 2

HCID 6558IsobutylamineHCID 67300640HCID 67300640, compound

Product 1

HCID 247726142-{[2-fluoro-6-(trifluoromethyl)benzoyl]amino}-N-isobutyl-4,4,6,6-tetramethyl-4,6-dihydrothieno[2,3-c]furan-3-carboxamide

Procedure

The title compound was prepared from the product of Example 45A and commercially available isobutylamine using the procedure described for Example 2B. 1H NMR (DMSO-d6, 300 MHz) δ 0.85 (d, J=6.8 Hz, 6H), 1.45 (s, 6H), 1.48 (s, 6H), 1.76 (sept, J=6.8 Hz, 1H), 2.99 (t, J=6.4 Hz, 2H), 7.67-7.81 (m, 3H), 8.05 (t, J=5.9 Hz, 1H), 11.49 (br s, 1H). MS (ESI+) m/z 487 (M+H)+. Anal. calcd. for C23H26F4N2O3S: C, 56.78; H, 5.39; N, 5.76. Found: C, 57.06; H, 5.57; N, 5.68.

Sources & evidence

ORD record
ord-38507a6bbf8e4143bfd6a41d1484bfe6
Source dataset
uspto-grants-2011_07
Patent number
US07985768B2

Reaction notes

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