(S)-2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetic acid → 1-[4-[2-(1H-Imidazol-1-yl)-ethoxy]-4-pyridin-3-yl-piperidin-1-yl]-2-[[(2S)-1-[(4-methoxy-2,6-dimethyl-phenyl)sulfonyl]-piperidin-2-yl]-methoxy]-ethanone

HRID 1881699Notes

Reaction equation

HRID 1881699 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[CH2:19][O:20][CH2:21][C:22](O)=[O:23])(=[O:12])=[O:11])=[C:5]([CH3:25])[CH:4]=1.[N:26]1([CH2:31][CH2:32][O:33][C:34]2([C:47]3[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=3)[CH2:39][CH2:38][N:37](C(OC(C)(C)C)=O)[CH2:36][CH2:35]2)[CH:30]=[CH:29][N:28]=[CH:27]1>>[N:26]1([CH2:31][CH2:32][O:33][C:34]2([C:47]3[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=3)[CH2:39][CH2:38][N:37]([C:22](=[O:23])[CH2:21][O:20][CH2:19][C@@H:14]3[CH2:15][CH2:16][CH2:17][CH2:18][N:13]3[S:10]([C:6]3[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH3:25])(=[O:11])=[O:12])[CH2:36][CH2:35]2)[CH:30]=[CH:29][N:28]=[CH:27]1

Participants

3

Reactant 2

HCID 57819715(S)-2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetic acidHCID 57916243tert-butyl 4-(2-(1H-imidazol-1-yl)ethoxy)-4-(pyridin-3-yl)piperidine-1-carboxylate

Product 1

HCID 444658871-[4-[2-(1H-Imidazol-1-yl)-ethoxy]-4-pyridin-3-yl-piperidin-1-yl]-2-[[(2S)-1-[(4-methoxy-2,6-dimethyl-phenyl)sulfonyl]-piperidin-2-yl]-methoxy]-ethanoneYield 60%

Procedure

The desired target compound was synthesized under reaction conditions analogously to the process described for Example 61 (see below) from (S)-2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetic acid [acid D] and tert-butyl 4-(2-(1H-imidazol-1-yl)ethoxy)-4-(pyridin-3-yl)piperidine-1-carboxylate [amine F]. Yield: 60%. MS, Rt=2.7 min, m/z=626.4 [MH]+

Workup

  1. customThe desired target compound was synthesized under reaction conditions analogously to the process

Sources & evidence

ORD record
ord-336faf86e07f4ba588ffe61d2714cf99
Source dataset
uspto-grants-2012_11
Patent number
US08318769B2

Reaction notes

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