Ammonium Acetate → HCID 58368675, compound

HRID 1192583Notes

Reaction equation

HRID 1192583 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([C:21]#[N:22])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:29].[Na+]>CO.C(#N)C>[NH2:29][CH:1]([C:4]1[N:5]=[C:6]([C:21]#[N:22])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:2]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58368600HCID 58368600, compound

Product 1

HCID 58368675HCID 58368675, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-acetyl-4-(3-fluorophenyl)isoquinoline-1-carbonitrile (4 mg, 0.01 mmol) and ammonium acetate (10.6 mg, 0.138 mmol) in methanol (0.078 mL) and acetonitrile (0.078 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling to room temperature, sodium cyanoborohydride (1.7 mg, 0.028 mmol) was added. The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature and quenched with sat. sodium bicarbonate, extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The residue was used directly in the next step. LCMS calculated for C18H15FN3 (M+H)+: m/z=292.1; Found: 292.1.

Workup

  1. temperatureAfter cooling to room temperature
  2. temperatureThe reaction was heated at 65° C. for another 4 hours
  3. temperaturecooled to room temperature
  4. customquenched with sat. sodium bicarbonate
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-3e5b3444c70844e6b004cb30410130ca
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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