3-Amino-1-propanol → 2-{[2-fluoro-6-(trifluoromethyl)benzoyl]amino}-N-(3-hydroxypropyl)-4,4,6,6-tetramethyl-4,6-dihydrothieno[2,3-c]furan-3-carboxamide

HRID 1015611Notes

Reaction equation

HRID 1015611 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].[OH:30][CH2:31][CH2:32][CH2:33][NH2:34]>>[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]([CH3:15])([CH3:14])[C:9]=2[C:8]=1[C:19]([NH:34][CH2:33][CH2:32][CH2:31][OH:30])=[O:20])=[O:5]

Participants

3

Reactant 2

HCID 90863-Amino-1-propanolHCID 67300640HCID 67300640, compound

Product 1

HCID 247727452-{[2-fluoro-6-(trifluoromethyl)benzoyl]amino}-N-(3-hydroxypropyl)-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 3-hydroxypropylamine using the procedure described for Example 2B. 1H NMR (DMSO-d6, 300 MHz) δ 1.44 (s, 6H), 1.47 (s, 6H), 1.56-1.65 (m, 2H), 3.18-3.25 (m, 2H), 3.37-3.44 (m, 2H), 4.43 (t, J=4.8 Hz, 1H), 7.67-7.80 (m, 3H), 8.01 (t, J=5.3 Hz, 1H), 11.57 (br s, 1H). MS (ESI+) m/z 489 (M+H)+. Anal. calcd. for C22H24F4N2O4S: C, 54.09; H, 4.95; N, 5.73. Found: C, 53.87; H, 4.86; N, 5.64.

Sources & evidence

ORD record
ord-ef961d7021be431b8ff72bc311b279e3
Source dataset
uspto-grants-2011_07
Patent number
US07985768B2

Reaction notes

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