Methanesulfonamide → HCID 86703595, compound

HRID 1849719Notes

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](O)=[O:38])=[C:35]([F:45])[CH:34]=1.COC[CH2:49][S:50]([NH2:53])(=[O:52])=[O:51].CS(N)(=O)=O>>[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]([NH:53][S:50]([CH3:49])(=[O:52])=[O:51])=[O:38])=[C:35]([F:45])[CH:34]=1

Participants

Reactant 4

HCID 72879Methanesulfonamide

HCID 189515062-Methoxyethane-1-sulfonamide

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

HCID 86703593HCID 86703593, compound

Product 1

HCID 86703595HCID 86703595, compoundYield 64%

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 methyl 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 (0.080 g, 64%): 1H NMR (300 MHz, DMSO-d6) δ 11.82 (br s, 1H), 7.10 (d, J=8.3 Hz, 1H), 6.83 (d, J=13.1 Hz, 1H), 4.81-4.72 (m, 1H), 3.29 (s, 3H), 2.59-2.54 (m, 1H), 2.25-2.19 (m, 1H), 2.17-2.05 (m, 1H), 2.04-1.92 (m, 1H), 1.91-1.78 (m, 1H), 1.61-1.48 (m, 1H), 1.46-1.17 (m, 4H), 0.97-0.80 (m, 3H), 0.67-0.60 (m, 2H); MS (ES+) m/z 368.09 (M+1).

Workup

customPurification by silica gel column chromatography (2:1 hexanes

Sources & evidence

ORD record: ord-d30c846538e041c8aeb4f1ece6442d34
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

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