Hydrochloric Acid → HCID 67198235, compound

HRID 544840Notes

Reaction equation

HRID 544840 reaction equation
[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[N:4]([C:10]1[N:15]=[CH:14][C:13]([NH2:16])=[CH:12][N:11]=1)[CH2:3][CH2:2]2.[C:17]1([CH2:23][C:24]([Cl:26])=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(OCC)C.Cl>C(O)C.C(N(CC)CC)C>[ClH:26].[N:1]12[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]1)[N:4]([C:10]1[N:15]=[CH:14][C:13]([NH:16][C:24](=[O:25])[CH2:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][N:11]=1)[CH2:3][CH2:2]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 7679Phenylacetyl chloride2×HCID 66630811HCID 66630811, compound

Product 1

HCID 67198235HCID 67198235, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 8471TriethylamineSolvent

Procedure

2-(1,4-Diaza-bicyclo[3.2.2]non-4-yl)-pyrimidin-5-ylamine (0.877 g, 4.00 mmol) and ethanol (50 ml) was mixed with phenylacetyl chloride (0.742 g, 4.8 mmol) and was stirred for 15 hours at room-temperature, followed by addition of phenylacetyl chloride (74 mg, 0.48 mmol) and stirring for 15 hours. Diethylether (30 ml) was added. The mixture was made alkaline by adding triethylamine (20 ml). The crude mixture was purified by silica gel chromatography, using a 10:1+1% dichloromethane:methanol+aqueous ammonia mixture as eluent. The corresponding hydrochloride was prepared by solving the free base in ethanol (10 ml, 99%) followed by addition of HCl in ethanol (2 ml, 3 M). Yield 710 mg (47%). LC-ESI−HRMS of [M+H]+ shows 338.1976 Da. Calc. 338.198085 Da, dev. −1.4 ppm.

Workup

  1. stirringstirring for 15 hours
  2. customThe crude mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-db582c615a794b9bab2aa8bbdcb9a84f
Source dataset
uspto-grants-2011_05
Patent number
US07935695B2

Reaction notes

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