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

HRID 1015598Notes

Reaction equation

HRID 1015598 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]([OH:21])=O)=[O:5].[CH:30]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH:30]1([NH:35][C:19]([C:8]2[C:9]3[C:13]([CH3:15])([CH3:14])[O:12][C:11]([CH3:17])([CH3:16])[C:10]=3[S:18][C:7]=2[NH:6][C:4](=[O:5])[C:3]2[C:22]([C:26]([F:29])([F:28])[F:27])=[CH:23][CH:24]=[CH:25][C:2]=2[F:1])=[O:21])[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 67300640HCID 67300640, compound

Product 1

HCID 24772613N-cyclopentyl-2-{[2-fluoro-6-(trifluoromethyl)benzoyl]amino}-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 cyclopentylamine by the procedure described for Example 2B. 1H NMR (DMSO-d6, 300 MHz) δ 1.43 (s, 6H), 1.47 (s, 6H), 1.43-1.50 (m, 4H), 1.55-1.66 (m, 2H), 1.74-1.82 (m, 2H), 4.02-4.14 (m, 1H), 7.67-7.77 (m, 3H), 8.04 (d, J=7.5 Hz, 1H), 11.53 (br s, 1H). MS (ESI+) m/z 499 (M+H)+. Anal. calcd. for C24H26F4N2O3S: C, 57.82; H, 5.26; N, 5.62. Found: C, 57.77; H, 5.32; N, 5.53.

Sources & evidence

ORD record
ord-848578c1999a47c0ae3b3229f0378659
Source dataset
uspto-grants-2011_07
Patent number
US07985768B2

Reaction notes

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