Methanesulfonamide → HCID 86703708, compound

HRID 1849821Notes

Reaction equation

[CH:1]12[CH2:6][CH:5]1[CH2:4][CH:3]([CH2:7][O:8][C:9]1[C:17]([CH:18]3[CH2:20][CH2:19]3)=[CH:16][C:12]([C:13](O)=[O:14])=[C:11]([F:21])[CH:10]=1)[CH2:2]2.CS(N)(=O)=O.[N:27]1([S:31]([NH2:34])(=[O:33])=[O:32])[CH2:30][CH2:29][CH2:28]1>>[N:27]1([S:31]([NH:34][C:13](=[O:14])[C:12]2[CH:16]=[C:17]([CH:18]3[CH2:19][CH2:20]3)[C:9]([O:8][CH2:7][CH:3]3[CH2:4][CH:5]4[CH:1]([CH2:6]4)[CH2:2]3)=[CH:10][C:11]=2[F:21])(=[O:33])=[O:32])[CH2:30][CH2:29][CH2:28]1

Participants

Reactant 3

HCID 72879Methanesulfonamide

HCID 450805661-Azetidinesulfonamide

HCID 86703709HCID 86703709, compound

Product 1

HCID 86703708HCID 86703708, compound

Procedure

Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace 4-(((1r,3r,5r,7r)-2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 4-(bicyclo[3.1.0]hexan-3-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid and to replace methanesulfonamide with azetidine-1-sulfonamide, the title compound was obtained as a white solid (0.037 g, 27%): 1H NMR (300 MHz, CDCl3) δ11.60 (br, s, 1H), 7.13 (d, J=8.31 Hz, 1H), 6.94 (d, J=12.98 Hz, 1H), 4.11-3.96 (m, 4H), 3.83 (d, J=7.42 Hz, 2H), 2.83-2.67 (m, 1H), 2.25-2.07 (m, 4H), 2.05-1.92 (m, 1H), 1.58-1.45 (m, 2H), 1.37-1.26 (m, 2H), 0.94-0.82 (m, 2H), 0.72-0.54 (m, 3H), 0.14-0.06 (m, 1H); MS (ES+) m/z 409.1 (M+1).

Sources & evidence

ORD record: ord-6c1c632c5860435f9f2b967b9b7193a4
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

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