Sodium Bicarbonate → HCID 178508291, compound

HRID 1710716Notes

Reaction equation

HRID 1710716 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH2:21])[C:11](N)=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.N([O-])=[O:23].[Na+].C([O-])(O)=O.[Na+]>Cl.O>[NH2:21][C:10]1[C:11]([OH:23])=[N:12][C:13]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[N:9]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 16070570HCID 16070570, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178508291HCID 178508291, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a cooled solution (0° C.) of 5-(3-fluorophenyl)-6-pyridin-4-ylpyrazine-2,3-diamine (Example 72, 100 mg, 0.36 mmol) in HCl 1N (1 mL) was added dropwise a solution of sodium nitrite (35 mg, 0.50 mmol) in water (0.6 mL). The reaction was stirred for 1 h at room temperature and after this period was driven to pH7 by addition of a NaHCO3 4% solution. The suspension was filtered to leave a solid which was purified by silica gel chromatography eluting with CH2Cl2/MeOH/NH3 (50:8:1) to afford the title compound (37 mg, 36%).

Workup

  1. filtrationThe suspension was filtered
  2. customto leave a solid which
  3. customwas purified by silica gel chromatography
  4. washeluting with CH2Cl2/MeOH/NH3 (50:8:1)

Sources & evidence

ORD record
ord-9a4ae1afa81d49ee880a1d0d875e3dd9
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

Loading…