Ammonium Acetate → HCID 58515929, compound

HRID 717840Notes

Reaction equation

HRID 717840 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[C:13]([Cl:19])=[CH:12][C:11]=2[C:20](=O)[CH3:21])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:29].[Na+]>CO.C(#N)C>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[C:13]([Cl:19])=[CH:12][C:11]=2[CH:20]([NH2:29])[CH3:21])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58516005HCID 58516005, compound

Product 1

HCID 58515929HCID 58515929, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-[5-(4-acetylpiperazin-1-yl)-8-chloroimidazo[1,5-a]pyridin-6-yl]ethanone (12.6 mg, 0.0393 mmol) (10010-158P) and ammonium acetate (30.3 mg, 0.393 mmol) in methanol (0.4 mL) and acetonitrile (0.4 mL) was heated at 65° C. in a sealed vial for 1 hour. The mixture was cooled to room temperature and sodium cyanoborohydride (7.40 mg, 0.118 mmol) was added. The reaction was heated at 65° C. overnight. The mixture was diluted with methanol and purified on preparative LCMS using pH 10 buffer to give the desired compound (11 mg, 89%). LCMS calculated for C15H21ClN5O (M+H)+: m/z=322.1. found: 321.9.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. temperatureThe reaction was heated at 65° C. overnight
  3. custompurified on preparative LCMS

Sources & evidence

ORD record
ord-c8d930139e6a48dab0a5232ab2f16181
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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