Hydrochloric Acid → Hydrochloric Acid

HRID 873429Notes

Reaction equation

HRID 873429 reaction equation
CC([N:5]([CH2:9][C:10]1[C:11](=[O:21])[NH:12][C:13]([CH:17]2[CH2:20][CH2:19][CH2:18]2)=[CH:14][C:15]=1[CH3:16])C(=O)[O-])(C)C.[ClH:22]>>[NH2:5][CH2:9][C:10]1[C:11](=[O:21])[NH:12][C:13]([CH:17]2[CH2:18][CH2:19][CH2:20]2)=[CH:14][C:15]=1[CH3:16].[ClH:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86677354HCID 86677354, compound

Product 2

HCID 313Hydrochloric AcidYield 90%HCID 67464880HCID 67464880, compound

Procedure

A solution of 1,1-dimethylethyl[(6-cyclobutyl-4-methyl-2-oxo-1,2-dihydro-3pyridinyl)methyl]carbamate (2.1 g, 7.2 mmol) in 4 N HCl (in 15 mL 1,4 dioxane) was heated to 60° C. for 1 h. The mixture was cooled to room temperature. The mixture was filtered and dried to give 3-(aminomethyl)-6-cyclobutyl-4-methyl-2(1H)-pyridinone as an HCl salt (1.95 g, 90%). LCMS MH+=193.1 1H NMR (400 MHz, DMSO-d6) δ 11.70 (br s, 1H), 8.01 (s, 3H), 6.04 (s, 1H), 3.74 (d, 2H), 3.32-3.39 (m, 1H), 2.22 (s, 3H), 2.17-2.20 (m, 2H), 2.06-2.11 (m, 2H), 1.85-1.95 (m, 1H), 1.71-1.79 (m, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. customdried

Sources & evidence

ORD record
ord-c40f3229bf07433bb91ebbb823da503c
Source dataset
uspto-grants-2015_03
Patent number
US08975291B2

Reaction notes

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