Cyclopropanesulfonamide → HCID 86703532, compound

HRID 1849666Notes

Reaction equation

[Cl:1][C:2]1[C:3]([O:12][CH2:13][C:14]2([C:18]([F:21])([F:20])[F:19])[CH2:17][CH2:16][CH2:15]2)=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].N1(S(N)(=O)=O)CCC1.[CH:30]1([S:33]([NH2:36])(=[O:35])=[O:34])[CH2:32][CH2:31]1>>[Cl:1][C:2]1[C:3]([O:12][CH2:13][C:14]2([C:18]([F:21])([F:19])[F:20])[CH2:15][CH2:16][CH2:17]2)=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([NH:36][S:33]([CH:30]1[CH2:32][CH2:31]1)(=[O:35])=[O:34])=[O:8]

Participants

Reactant 3

HCID 15765418Cyclopropanesulfonamide

HCID 450805661-Azetidinesulfonamide

HCID 86703529HCID 86703529, compound

Product 1

HCID 86703532HCID 86703532, compound

Procedure

Following the procedure as described in Example 218 step 5 and making variations as required to replace trans-4-((5-chloroadamantan-2-yl)oxy)-5-cyclopropyl-2-fluorobenzoic acid with 5-chloro-2-fluoro-4-((1-(trifluoromethyl)cyclobutyl)methoxy)benzoic acid and to replace azetidine-1-sulfonamide with cyclopropanesulfonamide, the title compound was obtained as colorless solid (0.04 g, 47%): 1H NMR (300 MHz, DMSO-d6) δ 12.10 (s, 1H), 7.78 (d, J=7.5 Hz, 1H), 7.39 (d, J=12.4 Hz, 1H), 4.41 (s, 2H), 3.12-3.03 (m, 1H), 2.37-2.27 (m, 2H), 2.18-2.09 (m, 3H), 2.01-1.92 (m, 1H), 1.15-1.11 (m, 4H); MS (ES+) m/z 430.0, 432.0 (M+1); MS (ES−) m/z 428.1, 430.1 (M−1).

Sources & evidence

ORD record: ord-0d658a420ab04e12968a811bc3cd209c
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

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