Hydrochloric Acid → methyl (S)-5-cyclobutoxy-6-(2-(4-hydroxypiperidin-4-yl)thiazol-4-yl)-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate

HRID 1051651Notes

Reaction equation

HRID 1051651 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][C:12]([C:16]2[S:17][CH:18]=[C:19]([C:21]3[C:22]([O:36][CH:37]4[CH2:40][CH2:39][CH2:38]4)=[C:23]4[C:28](=[CH:29][CH:30]=3)[N:27]([C:31]([O:33][CH3:34])=[O:32])[C@@H:26]([CH3:35])[CH2:25][CH2:24]4)[N:20]=2)(F)[CH2:11][CH2:10]1)=O)(C)(C)C.[O:41]1CCOCC1>>[CH:37]1([O:36][C:22]2[C:21]([C:19]3[N:20]=[C:16]([C:12]4([OH:41])[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]4)[S:17][CH:18]=3)=[CH:30][CH:29]=[C:28]3[C:23]=2[CH2:24][CH2:25][C@H:26]([CH3:35])[N:27]3[C:31]([O:33][CH3:34])=[O:32])[CH2:40][CH2:39][CH2:38]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 118075645(S)-methyl 6-(2-(1-(tert-butoxycarbonyl)-4-fluoropiperidin-4-yl)thiazol-4-yl)-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate

Product 1

HCID 131736100methyl (S)-5-cyclobutoxy-6-(2-(4-hydroxypiperidin-4-yl)thiazol-4-yl)-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate

Procedure

HCl (4 M in 1,4-dioxane, 0.32 mL, 1.28 mmol) was added to a solution of (S)-methyl 6-(2-(1-(tert-butoxycarbonyl)-4-fluoropiperidin-4-yl)thiazol-4-yl)-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate (0.072 g, 0.128 mmol) in 1,4-dioxane (0.5 mL), and the reaction mixture stirred at rt for 1 h. The reaction mixture was concentrated and the residue was purified by mass triggered preparatory HPLC. The product-containing fractions were combined and concentrated in a Genevac to afford the methyl (S)-5-cyclobutoxy-6-(2-(4-hydroxypiperidin-4-yl)thiazol-4-yl)-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate. MS (ESI, pos. ion) m/z 460 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by mass
  3. concentrationconcentrated in a Genevac

Sources & evidence

ORD record
ord-e8b85ba1bdb143338abd7ff52891ecd8
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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