Hydrochloric Acid → (2S,4S)-4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-N-methoxy-N-methylpiperidine-2-carboxamide dihydrochloride

HRID 876426Notes

Reaction equation

HRID 876426 reaction equation
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][C@H:21]4[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[C@H:23]([C:34](=[O:39])[N:35]([O:37][CH3:38])[CH3:36])[CH2:22]4)[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(Cl)(Cl)[Cl:41].[ClH:44]>CCOCC>[ClH:41].[ClH:44].[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][C@H:21]4[CH2:26][CH2:25][NH:24][C@H:23]([C:34]([N:35]([O:37][CH3:38])[CH3:36])=[O:39])[CH2:22]4)[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 86654359(2S,4S)-tert-butyl 4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-2-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

Product 1

HCID 86654360(2S,4S)-4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-N-methoxy-N-methylpiperidine-2-carboxamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the product from Step A (0.032 g, 0.0601 mmol) was added CHCl3 (0.600 mL) and HCl (0.451 mL, 1.80 mmol, 4.0M in dioxane). The mixture was stirred at ambient temperature for 9 hours, then diluted with Et2O (5 mL) and filtered. The solid was washed with Et2O and dried in vacuo. This provided 0.026 g (82%) of the desired product as a pale yellow solid. MS ESI (+) m/z 433.1 (M+1) detected.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with Et2O
  3. customdried in vacuo

Sources & evidence

ORD record
ord-961d8a6e37b949a98dcbff1c407e48eb
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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