Hydrochloric Acid → Hydrochloric Acid

HRID 62377Notes

Reaction equation

HRID 62377 reaction equation
[CH:1]1([C:5]2[NH:10][C:9](=[O:11])[C:8]([CH2:12][NH:13]C(=O)OC(C)(C)C)=[C:7]([CH3:21])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[ClH:22]>>[NH2:13][CH2:12][C:8]1[C:9](=[O:11])[NH:10][C:5]([CH:1]2[CH2:2][CH2:3][CH2:4]2)=[CH:6][C:7]=1[CH3:21].[ClH:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 679517421,1-Dimethylethyl [(6-cyclobutyl-4-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]carbamate

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-0071d3c6aef14222a1e93555767a6d19
Source dataset
uspto-grants-2016_09
Patent number
US09446041B2

Reaction notes

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