Hydrochloric Acid → HCID 71466164, compound

HRID 572657Notes

Reaction equation

HRID 572657 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[O:18][N:17]=[C:16]([C:19]3[CH:24]=[C:23]([C:25](=[O:37])[NH:26][CH2:27][C:28]4[CH:33]=[CH:32][C:31]([F:34])=[C:30]([O:35][CH3:36])[CH:29]=4)[N:22]=[C:21]([CH3:38])[N:20]=3)[CH2:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:39]>O1CCOCC1>[ClH:39].[F:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][NH:26][C:25]([C:23]2[CH:24]=[C:19]([C:16]3[CH2:15][CH:14]([CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[O:18][N:17]=3)[N:20]=[C:21]([CH3:38])[N:22]=2)=[O:37])=[CH:29][C:30]=1[O:35][CH3:36]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71466552HCID 71466552, compound

Product 1

HCID 71466164HCID 71466164, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl-4-(3-(6-(4-fluoro-3-methoxybenzylcarbamoyl)-2-methylpyrimidin-4-yl)-4,5-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.3 g, 0.569 mmol, G.1.18) was dissolved in 4N 1,4-dioxane.HCl (5 mL) and stirred at RT for about 1 h. Excess solvent was removed in vacuo and the crude material was triturated with ether (2×10 mL) to afford N-(4-fluoro-3-methoxybenzyl)-2-methyl-6-(5-(piperidin-4-yl)-4,5-dihydroisoxazol-3-yl)pyrimidine-4-carboxamide hydrochloride as a white solid 0.2 g (82%). LC/MS (Table 1, method e) Rt=2.53 min; MS m/z 428.3 (M+H)+.

Workup

  1. customExcess solvent was removed in vacuo
  2. customthe crude material was triturated with ether (2×10 mL)

Sources & evidence

ORD record
ord-a19ab1a9b5de4c139f09cb62c9182267
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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