Sodium Nitrite → HCID 58075184, compound

HRID 1186778Notes

Reaction equation

HRID 1186778 reaction equation
N([O-])=O.[Na+].C(O)(=[O:7])C.N[C:10]1[CH:11]=[CH:12][C:13]([N:16]2[CH2:20][C:19]3[CH2:21][N:22]([C:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[C:32]([F:35])([F:34])[F:33])=[O:25])[CH2:23][C:18]=3[CH2:17]2)=[N:14][CH:15]=1>S(=O)(=O)(O)O.C(O)(=O)C>[OH:7][C:10]1[CH:11]=[CH:12][C:13]([N:16]2[CH2:20][C:19]3[CH2:21][N:22]([C:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[C:32]([F:35])([F:34])[F:33])=[O:25])[CH2:23][C:18]=3[CH2:17]2)=[N:14][CH:15]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 66710426HCID 66710426, compound

Product 1

HCID 58075184HCID 58075184, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

Sodium nitrite (106.1 mg, 1.537 mmol) was dissolved at 0° C. in 1.84 ml of conc. sulfuric acid. Subsequently, [5-(5-aminopyridin-2-yl)-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrol-2-yl](2-trifluoromethylphenyl)methanone acetate (523 mg, 1.2 mmol), dissolved in 8 ml of acetic acid, was added dropwise, the cooling bath was removed and stirring was continued for 1 h. The reaction solution was added dropwise to 50 ml of boiling water and stirred under reflux for 5 h. After cooling, the mixture was admixed with ethyl acetate and filtered off from the residue, the water phase was adjusted to pH 4 with sodium hydrogencarbonate solution, and the organic phase was removed and concentrated. Yield: 181 mg (40%), M+H+: 376.11.

Workup

  1. additionwas added dropwise
  2. customthe cooling bath was removed
  3. additionThe reaction solution was added dropwise to 50 ml of boiling water
  4. stirringstirred
  5. temperatureunder reflux for 5 h
  6. temperatureAfter cooling
  7. filtrationfiltered off from the residue
  8. customthe organic phase was removed
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ec5467746f5543e985f67896a8c9fa17
Source dataset
uspto-grants-2014_03
Patent number
US08673917B2

Reaction notes

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