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

HRID 1015601Notes

Reaction equation

HRID 1015601 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].[NH2:30][CH2:31][CH:32]1[CH2:34][CH2:33]1>>[CH:32]1([CH2:31][NH:30][C:19]([C:8]2[C:9]3[C:13]([CH3:14])([CH3:15])[O:12][C:11]([CH3:16])([CH3:17])[C:10]=3[S:18][C:7]=2[NH:6][C:4](=[O:5])[C:3]2[C:22]([C:26]([F:28])([F:29])[F:27])=[CH:23][CH:24]=[CH:25][C:2]=2[F:1])=[O:20])[CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 75646CyclopropanemethanamineHCID 67300640HCID 67300640, compound

Product 1

HCID 24772678N-(cyclopropylmethyl)-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 aminomethylcyclopropane using the procedure described for Example 2B. 1H NMR (DMSO-d6, 300 MHz) δ 0.15-0.20 (m, 2H), 0.35-0.41 (m, 2H), 0.91-1.01 (m, 1H), 1.46 (s, 6H), 1.48 (s, 6H), 3.03 (dd, J=6.1, 6.0 Hz, 2H), 7.67-7.80 (m, 3H), 8.11 (t, J=5.6 Hz, 1H), 11.56 (br s, 1H). MS (ESI+) m/z 485 (M+H)+.

Sources & evidence

ORD record
ord-fcb08d57cc5d4ae6a93bfa0baea3d496
Source dataset
uspto-grants-2011_07
Patent number
US07985768B2

Reaction notes

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