Tetrahydro-3-furanmethanol → HCID 66799721, compound

HRID 589781Notes

Reaction equation

HRID 589781 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([OH:19])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:23])[C:6]=2[CH:24]=1.O[CH2:26][CH:27]1[CH2:31][CH2:30][O:29][CH2:28]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([O:19][CH2:26][CH:27]3[CH2:31][CH2:30][O:29][CH2:28]3)=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:23])[C:6]=2[CH:24]=1

Participants

3

Reactant 2

HCID 139980Tetrahydro-3-furanmethanolHCID 569413063-{[(5-Chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acid2×

Product 1

HCID 66799721HCID 66799721, compoundYield 64%

Procedure

The product was prepared from 3-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acid (21 mg, 0.055 mmol) (Intermediate 19) and 3-hydroxymethyltetrahydrofuran (10.2 mg, 0.100 mmol) according to the General Procedure 7, described in Example 107. The title compound was obtained in 64% yield (16.5 mg). 1H NMR (500 MHz, CDCl3) δ ppm 1.67 (dddd, J=12.56, 7.90, 7.00, 5.96 Hz, 1 H) 2.06 (dddd, J=12.56, 8.61, 7.70, 5.54 Hz, 1 H) 2.45 (s, 3 H) 2.61-2.70 (m, 1 H) 3.62 (dd, J=8.86, 5.45 Hz, 1 H) 3.77 (ddd, J=8.61, 7.70, 7.00 Hz, 1 H) 3.86 (dd, J=8.86, 7.06 Hz, 1 H) 3.88 (ddd, J=8.61, 7.90, 5.54 Hz, 1 H) 4.19 (dd, J=10.89, 7.81 Hz, 1 H) 4.28 (dd, J=10.89, 6.49 Hz, 1 H) 7.02 (s, 1 H) 7.37 (dd, J=8.00, 7.66 Hz, 1 H) 7.43 (ddd, J=8.06, 2.32, 1.22 Hz, 1 H) 7.44 (dd, J=8.67, 1.95 Hz, 1 H) 7.72 (dd, J=8.67, 0.53 Hz, 1 H) 7.71 (dd, J=1.95, 0.53 Hz, 1 H) 7.71-7.72 (m, 1 H) 7.82 (ddd, J=7.66, 1.55, 1.22 Hz, 1 H). MS (ESI+) m/z 466 [M+H]+.

Sources & evidence

ORD record
ord-e632dc55c8d24d32aae3d8718286882f
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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