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

HRID 1849561Notes

Reaction equation

HRID 1849561 reaction equation
C12(COC3C(C4CC4)=CC(C(O)=O)=C(F)C=3)CC3CC(CC(C3)C1)C2.[C:26]12([CH2:36][O:37][C:38]3[C:46]([Cl:47])=[CH:45][C:41]([C:42](O)=[O:43])=[C:40]([F:48])[CH:39]=3)[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2.CS(N)(=O)=O.[CH3:54][O:55][C:56]1[CH:72]=[CH:71][C:59]([CH2:60][O:61][C@H:62]2[CH2:66][CH2:65][N:64]([S:67]([NH2:70])(=[O:69])=[O:68])[CH2:63]2)=[CH:58][CH:57]=1>>[C:26]12([CH2:36][O:37][C:38]3[C:46]([Cl:47])=[CH:45][C:41]([C:42]([NH:70][S:67]([N:64]4[CH2:65][CH2:66][C@H:62]([O:61][CH2:60][C:59]5[CH:71]=[CH:72][C:56]([O:55][CH3:54])=[CH:57][CH:58]=5)[CH2:63]4)(=[O:69])=[O:68])=[O:43])=[C:40]([F:48])[CH:39]=3)[CH2:27][CH:28]3[CH2:34][CH:32]([CH2:31][CH:30]([CH2:29]3)[CH2:35]1)[CH2:33]2

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 867028594-(Adamantan-1-ylmethoxy)-5-chloro-2-fluorobenzoic acidHCID 867028614-(Adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 86702905(S)-3-((4-methoxybenzyl)oxy)pyrrolidine-1-sulfonamide

Product 1

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

Procedure

Following the procedure as described in Example 50 step 5 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid with 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluorobenzoic acid and methanesulfonamide with (S)-3-((4-methoxybenzyl)oxy)pyrrolidine-1-sulfonamide, the title compound was obtained as colorless solid (0.17 g, 47%): MS (ES+) m/z 607.1, 609.1 (M+1); MS (ES−) m/z 605.3, 607.3 (M−1).

Sources & evidence

ORD record
ord-34396c7d41cd446abc3740be22b83ad0
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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