2-Methoxyethane-1-sulfonamide → HCID 86703596, compound

HRID 1849720Notes

Reaction equation

C12(COC3C(C4CC4)=CC(C(O)=O)=CN=3)CC3CC(CC(C3)C1)C2.[C@@H:25]12[CH2:31][C@@H:28]([CH2:29][CH2:30]1)[CH2:27][C@H:26]2[O:32][C:33]1[C:41]([CH:42]2[CH2:44][CH2:43]2)=[CH:40][C:36]([C:37]([OH:39])=O)=[C:35]([F:45])[CH:34]=1.COCCS(N)(=O)=O.[N:54]1([S:58]([NH2:61])(=[O:60])=[O:59])[CH2:57][CH2:56][CH2:55]1>>[N:54]1([S:58]([NH:61][C:37](=[O:39])[C:36]2[CH:40]=[C:41]([CH:42]3[CH2:43][CH2:44]3)[C:33]([O:32][C@@H:26]3[CH2:27][C@H:28]4[CH2:31][C@@H:25]3[CH2:30][CH2:29]4)=[CH:34][C:35]=2[F:45])(=[O:60])=[O:59])[CH2:57][CH2:56][CH2:55]1

Participants

Reactant 4

HCID 189515062-Methoxyethane-1-sulfonamide

HCID 450805661-Azetidinesulfonamide

HCID 867029246-(Adamantan-1-ylmethoxy)-5-cyclopropylnicotinic acid

HCID 86703593HCID 86703593, compound

Product 1

HCID 86703596HCID 86703596, compoundYield 79%

Procedure

Following the procedure as described in Example 271 and making variations as required to replace 6-(adamantan-1-ylmethoxy)-5-cyclopropylnicotinic acid with 4-((1S,2R,4R)-bicyclo[2.2.1]heptan-2-yloxy)-5-cyclopropyl-2-fluorobenzoic acid and to replace 2-methoxyethanesulfonamide with azetidine-1-sulfonamide. Purification by silica gel column chromatography (2:1 hexanes:ethyl acetate (+0.2% acetic acid v/v)) gave the title compound as a colorless solid (0.11 g, 79%): 1H NMR (300 MHz, DMSO-d6) δ 11.54 (br s, 1H), 7.10 (d, J=8.3 Hz, 1H), 6.84 (d, J=13.1 Hz, 1H), 4.82-4.73 (m, 1H), 4.00 (t, J=7.6 Hz, 4H), 2.60-2.54 (m, 1H), 2.25-2.19 (m, 1H), 2.18-2.05 (m, 3H), 2.04-1.93 (m, 1H), 1.91-1.80 (m, 1H), 1.61-1.49 (m, 1H), 1.46-1.17 (m, 4H), 0.98-0.81 (m, 3H), 0.68-0.60 (m, 2H); MS (ES+) m/z 409.1 (M+1).

Workup

customPurification by silica gel column chromatography (2:1 hexanes

Sources & evidence

ORD record: ord-e127ba566a2341fb84fdecc7a1cbbcc7
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

Loading…