Methanesulfonyl chloride → 4-(adamantan-1-ylmethoxy)-N-(cyclobutylsulfonyl)-5-cyclopropyl-2-fluorobenzamide

HRID 1849625Notes

Reaction equation

HRID 1849625 reaction equation
C12(COC3C=CC(C(N)=O)=CC=3C3C(OC)=NC=CC=3)CC3CC(CC(C3)C1)C2.[C:30]12([CH2:40][O:41][C:42]3[C:50]([CH:51]4[CH2:53][CH2:52]4)=[CH:49][C:45]([C:46]([NH2:48])=[O:47])=[C:44]([F:54])[CH:43]=3)[CH2:39][CH:34]3[CH2:35][CH:36]([CH2:38][CH:32]([CH2:33]3)[CH2:31]1)[CH2:37]2.CS(Cl)(=O)=O.[CH:60]1([S:64](Cl)(=[O:66])=[O:65])[CH2:63][CH2:62][CH2:61]1>>[C:30]12([CH2:40][O:41][C:42]3[C:50]([CH:51]4[CH2:52][CH2:53]4)=[CH:49][C:45]([C:46]([NH:48][S:64]([CH:60]4[CH2:63][CH2:62][CH2:61]4)(=[O:66])=[O:65])=[O:47])=[C:44]([F:54])[CH:43]=3)[CH2:37][CH:36]3[CH2:38][CH:32]([CH2:33][CH:34]([CH2:35]3)[CH2:39]1)[CH2:31]2

Participants

5

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 22636930Cyclobutanesulfonyl chlorideHCID 867028454-(Adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzamideHCID 867034794-(Adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzamide

Product 1

HCID 867034814-(adamantan-1-ylmethoxy)-N-(cyclobutylsulfonyl)-5-cyclopropyl-2-fluorobenzamide

Procedure

Following the procedure as described in Example 38 step 4 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzamide with 4-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzamide and to replace methanesulfonyl chloride with cyclobutanesulfonyl chloride, the title compound was obtained as a colorless solid (0.05 g, 10%): 1H NMR (300 MHz, CDCl3) δ8.57-8.44 (m, 1H), 7.60-7.52 (m, 1H), 6.61-6.48 (m, 1H), 4.61-4.46 (m, 1H), 3.55 (s, 2H), 2.74-2.56 (m, 2H), 2.45-2.29 (m, 2H), 2.12-1.97 (m, 6H), 1.84-1.64 (m, 12H), 0.99-0.88 (m, 2H), 0.71-0.58 (m, 2H); MS (ES+) m/z 462.2 (M+1).

Sources & evidence

ORD record
ord-1b7725d39114443ab61c45b5423787db
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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