Hydrochloric Acid → HCID 68183124, compound

HRID 1615541Notes

Reaction equation

HRID 1615541 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH:11]([C:19]1[N:20]=[C:21]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[S:22][C:23]=1[C:24]([OH:26])=[O:25])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[ClH:18].[NH2:8][CH2:9][CH2:10][CH:11]([C:19]1[N:20]=[C:21]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[S:22][C:23]=1[C:24]([OH:26])=[O:25])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68183233HCID 68183233, compound

Product 1

HCID 68183124HCID 68183124, compoundYield 215.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{3-[(tert-butoxycarbonyl)amino]-1-(4-chlorophenyl)propyl}-2-(morpholin-4-yl)-1,3-thiazole-5-carboxylic acid (0.304 g, 0.631 mmol) in DCM (5.9 mL) was added a solution of hydrogen chloride in dioxane (4 M, 3.1 mL, 12 mmol) and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated and the residue was then azeotroped with toluene and dried under vacuum to give the product (0.284 g, 108%) which was used directly in the next step. LCMS: (AA) ES+ 382, 384.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was then azeotroped with toluene
  3. customdried under vacuum

Sources & evidence

ORD record
ord-fcab611687ca45c39bf4315391908cc1
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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