tert-Butyl (3S)-3-(hydroxymethyl)piperidine-1-carboxylate → (S)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoro-8-(piperidin-3-ylmethoxy)quinoline

HRID 2035619Notes

Reaction equation

HRID 2035619 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1.[N:16]1[N:17]=[C:18]([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[C:28](O)[CH:29]=[C:30]([F:35])[CH:31]=3)[N:26]=2)[N:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=12>>[N:16]1[N:17]=[C:18]([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[C:28]([O:1][CH2:2][C@H:3]4[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]4)[CH:29]=[C:30]([F:35])[CH:31]=3)[N:26]=2)[N:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=12

Participants

3

Reactant 2

HCID 1514448tert-Butyl (3S)-3-(hydroxymethyl)piperidine-1-carboxylateHCID 1363378052-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-ol

Product 1

HCID 58303761(S)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoro-8-(piperidin-3-ylmethoxy)quinoline

Procedure

Prepared as described in Example 16 using (S)-tert-butyl 3-(hydroxymethyl)piperidine-1-carboxylate in place of tert-butyl 3-(hydroxymethyl)piperidine-1-carboxylate, and 2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-ol in place of 2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-quinolin-8-ol. MS ESI (+) m/z 378.2 (M+1) detected.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-4906df0aaa4e4712891d73a7791dbd96
Source dataset
uspto-grants-2013_11
Patent number
US08575145B2

Reaction notes

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