Cyclopropanesulfonamide → HCID 178523996, compound

HRID 1849680Notes

Reaction equation

HRID 1849680 reaction equation
[CH:1]1([C:4]2[C:5]([O:14][CH2:15][C@H:16]3[CH2:21][CH2:20][C@@H:19]([C:22]([F:25])([F:24])[F:23])[CH2:18][CH2:17]3)=[CH:6][C:7]([F:13])=[C:8]([CH:12]=2)[C:9]([OH:11])=O)[CH2:3][CH2:2]1.N1(S(N)(=O)=O)CCC1.[CH:34]1([S:37]([NH2:40])(=[O:39])=[O:38])[CH2:36][CH2:35]1>>[CH:1]1([C:4]2[C:5]([O:14][CH2:15][C@H:16]3[CH2:17][CH2:18][C@@H:19]([C:22]([F:25])([F:23])[F:24])[CH2:20][CH2:21]3)=[CH:6][C:7]([F:13])=[C:8]([CH:12]=2)[C:9]([NH:40][S:37]([CH:34]2[CH2:36][CH2:35]2)(=[O:39])=[O:38])=[O:11])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 15765418CyclopropanesulfonamideHCID 450805661-AzetidinesulfonamideHCID 178524104HCID 178524104, compound

Product 1

HCID 178523996HCID 178523996, 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 cis-5-cyclopropyl-2-fluoro-4-((4-(trifluoromethyl)cyclohexyl)-methoxy)benzoic acid and to replace azetidine-1-sulfonamide with cyclopropanesulfonamide, the title compound was obtained as colorless solid (0.11 g, 79%): 1H NMR (300 MHz, DMSO-d6) δ 11.82 (s, 1H), 7.13 (d, J=8.3 Hz, 1H), 7.04 (d, J=13.1 Hz, 1H), 4.06 (d, J=7.1 Hz, 2H), 3.11-3.03 (m, 1H), 2.42-2.26 (m, 1H), 2.14 (brs, 1H), 2.06-1.97 (m, 1H), 1.74-1.56 (m, 8H), 1.13-1.09 (m, 4H), 0.91-0.85 (m, 2H), 0.69-0.64 (m, 2H); MS (ES+) m/z 464.1 (M+1); MS (ES−) m/z 462.2 (M−1).

Sources & evidence

ORD record
ord-3d7187e075eb47b9872b1683fb79abd5
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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