Prop-2-ynylamine hydrochloride → 2-{[2-fluoro-6-(trifluoromethyl)benzoyl]amino}-4,4,6,6-tetramethyl-N-prop-2-ynyl-4,6-dihydrothieno[2,3-c]furan-3-carboxamide

HRID 1015606Notes

Reaction equation

HRID 1015606 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].Cl.[CH2:31]([NH2:34])[C:32]#[CH:33]>>[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:28])([F:29])[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]([CH3:14])([CH3:15])[C:9]=2[C:8]=1[C:19]([NH:34][CH2:31][C:32]#[CH:33])=[O:21])=[O:5]

Participants

3

Reactant 2

HCID 11205720Prop-2-ynylamine hydrochlorideHCID 67300640HCID 67300640, compound

Product 1

HCID 247726822-{[2-fluoro-6-(trifluoromethyl)benzoyl]amino}-4,4,6,6-tetramethyl-N-prop-2-ynyl-4,6-dihydrothieno[2,3-c]furan-3-carboxamide

Procedure

The title compound was prepared from the product of Example 45A and commercially available propargylamine hydrochloride using the procedure described for Example 2B. 1H NMR (DMSO-d6, 300 MHz) δ 1.44 (s. 6H), 1.48 (s, 6H), 3.06-3.08 (m, 1H), 3.90-3.93 (m, 2H), 7.65-7.81 (m, 3H), 8.55 (t, J=5.6 Hz, 1H), 11.58 (br s, 1H). MS (ESI+) m/z 469 (M+H)+. Anal. calcd. for C22H20F4N2O3S: C, 56.40; H, 4.30; N, 5.98. Found: C, 56.36; H, 4.27; N, 5.94.

Sources & evidence

ORD record
ord-baaf7b6c7e8844f8962d07f8959e7728
Source dataset
uspto-grants-2011_07
Patent number
US07985768B2

Reaction notes

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