Ammonium Acetate → HCID 178427932, compound

HRID 510844Notes

Reaction equation

HRID 510844 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[NH:13][N:12]=[N:11][N:10]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[C:4]([C:21](=O)[CH3:22])[CH:3]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:30].[Na+]>CO.C(#N)C>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[NH:13][N:12]=[N:11][N:10]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[C:4]([CH:21]([NH2:30])[CH3:22])[CH:3]=1

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 178466679HCID 178466679, compound

Product 1

HCID 178427932HCID 178427932, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-[4-chloro-3′-fluoro-5-methyl-6-(1H-tetrazol-5-yl)biphenyl-2-yl]ethanone (85 mg, 0.26 mmol), ammonium acetate (198 mg, 2.57 mmol) and sodium cyanoborohydride (32 mg, 0.51 mmol) in methanol (0.9 mL) and acetonitrile (0.9 mL) was heated at 65° C. overnight in a sealed tube. The mixture was cooled to room temperature and quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The crude product was used directly in next step (45 mg, 53%). LCMS calculated for C6H13ClFN4 (M−NH2)+: m/z=315.1. found: 315.1.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched with saturated sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-38bcf8ee9d8c4375827615085c235857
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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