1-Azetidinesulfonamide → N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluoro-4-(spiro[2.5]octan-6-yloxy)benzamide

HRID 1849920Notes

Reaction equation

HRID 1849920 reaction equation
ClC1C(OC2CCC(=O)CC2)=CC(F)=C(C=1)C(O)=O.[CH:20]1([C:23]2[C:24]([O:33][CH:34]3[CH2:41][CH2:40][C:37]4([CH2:39][CH2:38]4)[CH2:36][CH2:35]3)=[CH:25][C:26]([F:32])=[C:27]([CH:31]=2)[C:28]([OH:30])=O)[CH2:22][CH2:21]1.[N:42]1([S:46]([NH2:49])(=[O:48])=[O:47])[CH2:45][CH2:44][CH2:43]1>CO>[N:42]1([S:46]([NH:49][C:28](=[O:30])[C:27]2[CH:31]=[C:23]([CH:20]3[CH2:21][CH2:22]3)[C:24]([O:33][CH:34]3[CH2:35][CH2:36][C:37]4([CH2:38][CH2:39]4)[CH2:40][CH2:41]3)=[CH:25][C:26]=2[F:32])(=[O:48])=[O:47])[CH2:45][CH2:44][CH2:43]1

Participants

5

Reactant 3

HCID 450805661-AzetidinesulfonamideHCID 867036865-Chloro-2-fluoro-4-((4-oxocyclohexyl)oxy)benzoic acidHCID 867037995-Cyclopropyl-2-fluoro-4-(spiro[2.5]octan-6-yloxy)benzoic acid

Product 1

HCID 86703800N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluoro-4-(spiro[2.5]octan-6-yloxy)benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the procedure as described in Example 357 Step 4 and making non-critical variations to replace 5-chloro-2-fluoro-4-((4-oxocyclohexyl)oxy)benzoic acid with 5-cyclopropyl-2-fluoro-4-(spiro[2.5]octan-6-yloxy)benzoic acid and methanol with azetidine-1-sulfonamide, the title compound was obtained as a colorless solid (0.029 g, 12% yield): 1H NMR (300 MHz, DMSO-d6) δ11.57 (br s, 1H), 7.11 (d, J=8.4 Hz, 1H), 7.01 (d, J=13.2 Hz, 1H), 4.67-4.61 (m, 1H), 4.00 (t, J=7.7 Hz, 4H), 2.17-1.98 (m, 3H), 1.90-1.83 (m, 2H), 1.72-1.61 (m, 2H), 1.49-1.29 (m, 4H), 0.90-0.84 (m, 2H), 0.68-0.63 (m, 2H), 0.30-0.19 (m, 4H); MS (ES−) m/z 421.15 (M−1).

Sources & evidence

ORD record
ord-7e17f24082ce4991a763c3a8a8e43fce
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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