Methanesulfonamide → 5-cyclopropyl-2-fluoro-N-(methylsulfonyl)-4-(spiro[2.5]octan-6-yloxy)benzamide

HRID 1849921Notes

Reaction equation

HRID 1849921 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](O)=[O:29])[CH2:22][CH2:21]1.[CH3:42][S:43]([NH2:46])(=[O:45])=[O:44]>CO>[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]([NH:46][S:43]([CH3:42])(=[O:45])=[O:44])=[O:29])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 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 867038015-cyclopropyl-2-fluoro-N-(methylsulfonyl)-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 methanesulfonamide, the title compound was obtained as a colorless solid (0.121 g, 53% yield): 1H NMR (300 MHz, CDCl3) δ8.69 (d, J=16.2 Hz, 1H), 7.55 (d, J=9.2 Hz, 1H), 6.58 (d, J=14.8 Hz, 1H), 4.49-4.42 (m, 1H), 3.39 (s, 3H), 2.11-1.77 (m, 5H), 1.54-1.21 (m, 4H), 0.96-0.89 (m, 2H), 0.67-0.61 (m, 2H), 0.34-0.27 (m, 4H); MS (ES−) m/z 380.20 (M−1).

Sources & evidence

ORD record
ord-1f60f5f27d9240d3b6e38816b585987d
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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