4-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-(((S)-3-((4-methoxybenzyl)oxy)pyrrolidin-1-yl)sulfonyl)benzamide → (S)-4-(cyclohexylmethoxy)-5-cyclopropyl-2-fluoro-N-((3-hydroxypyrrolidin-1-yl)sulfonyl)benzamide

HRID 1849631Notes

Reaction equation

HRID 1849631 reaction equation
C12(COC3C(Cl)=CC(C(NS(N4CC[C@H](OCC5C=CC(OC)=CC=5)C4)(=O)=O)=O)=C(F)C=3)CC3CC(CC(C3)C1)C2.[CH:42]1([CH2:48][O:49][C:50]2[C:76]([CH:77]3[CH2:79][CH2:78]3)=[CH:75][C:53]([C:54]([NH:56][S:57]([N:60]3[CH2:64][CH2:63][C@H:62]([O:65]CC4C=CC(OC)=CC=4)[CH2:61]3)(=[O:59])=[O:58])=[O:55])=[C:52]([F:80])[CH:51]=2)[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>>[CH:42]1([CH2:48][O:49][C:50]2[C:76]([CH:77]3[CH2:78][CH2:79]3)=[CH:75][C:53]([C:54]([NH:56][S:57]([N:60]3[CH2:64][CH2:63][C@H:62]([OH:65])[CH2:61]3)(=[O:58])=[O:59])=[O:55])=[C:52]([F:80])[CH:51]=2)[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]1

Participants

3

Reactant 2

HCID 867029064-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-(((S)-3-((4-methoxybenzyl)oxy)pyrrolidin-1-yl)sulfonyl)benzamideHCID 86703490(S)-4-(cyclohexylmethoxy)-5-cyclopropyl-2-fluoro-N-((3-((4-methoxybenzyl)oxy)pyrrolidin-1-yl)sulfonyl)benzamide

Product 1

HCID 86703489(S)-4-(cyclohexylmethoxy)-5-cyclopropyl-2-fluoro-N-((3-hydroxypyrrolidin-1-yl)sulfonyl)benzamide

Procedure

Following the procedure as described in Example 124 step 3 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-(((S)-3-((4-methoxybenzyl)oxy)pyrrolidin-1-yl)sulfonyl)benzamide with (S)-4-(cyclohexylmethoxy)-5-cyclopropyl-2-fluoro-N-((3-((4-methoxybenzyl)oxy)pyrrolidin-1-yl)sulfonyl)benzamide, the title compound was obtained as colorless solid (0.14 g, 78%): 1H NMR (300 MHz, CDCl3) δ 8.86-8.76 (m, 1H), 7.58-7.46 (m, 1H), 6.63-6.48 (m, 1H), 4.55-4.35 (m, 1H), 3.92-3.77 (m, 3H), 3.71-3.59 (m, 3H), 2.48 (br s, 1H), 2.13-1.96 (m, 3H), 1.95-1.67 (m, 6H), 1.42-1.02 (m, 5H), 0.98-0.85 (m, 2H), 0.69-0.57 (m, 2H); MS (ES+) m/z 441.1 (M+1).

Sources & evidence

ORD record
ord-be39a290c93b4757be7da6c60ea9afdc
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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