Sodium Nitrite → HCID 67071581, compound

HRID 1260532Notes

Reaction equation

HRID 1260532 reaction equation
N([O-])=O.[Na+].FC(F)(F)C(O)=[O:8].N[C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C@@H:28]([NH:30][C:31](=[O:33])[CH3:32])[CH3:29])=[CH:22][CH:21]=2)=[N:17][CH:18]=1>S(=O)(=O)(O)O.C(O)(=O)C>[OH:8][C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C@@H:28]([NH:30][C:31](=[O:33])[CH3:32])[CH3:29])=[CH:22][CH:21]=2)=[N:17][CH:18]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 67071610HCID 67071610, compound

Product 1

HCID 67071581HCID 67071581, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

Sodium nitrite (154 mg, 2.23 mmol) was dissolved in 2.68 ml of concentrated sulfuric acid at 0° C. Then, N—{(S)-3-[4-(5-aminopyridin-2-yloxy)phenyl]-1-methylpropyl}-acetamide trifluoroacetate (832 mg, 2.01 mmol) in 5 ml of acetic acid was slowly added dropwise. After 1 h the ice bath was removed and stirring was continued for an hour. The reaction mixture was added dropwise to 100 ml of boiling water, the mixture was stirred for 1 h and, after cooling, extracted with ethyl acetate. The precipitated solid was filtered off and the filtrate was concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 153 mg (37%), M+H+: 301.13.

Workup

  1. customAfter 1 h the ice bath was removed
  2. waitwas continued for an hour
  3. additionThe reaction mixture was added dropwise to 100 ml of boiling water
  4. stirringthe mixture was stirred for 1 h
  5. temperatureafter cooling
  6. extractionextracted with ethyl acetate
  7. filtrationThe precipitated solid was filtered off
  8. concentrationthe filtrate was concentrated
  9. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-b755a82068f44851be8a484490910993
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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