Sodium Nitrite → HCID 59833795, compound

HRID 270712Notes

Reaction equation

HRID 270712 reaction equation
N[C:2]1[C:3]([C:14]2[CH:15]=[C:16]([NH:21][C:22](=[O:33])[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[CH:17]=[CH:18][C:19]=2[Cl:20])=[CH:4][C:5]2[CH:10]=[N:9][C:8]([S:11][CH3:12])=[N:7][C:6]=2[N:13]=1.N([O-])=[O:35].[Na+]>C(O)(C(F)(F)F)=O>[Cl:20][C:19]1[CH:18]=[CH:17][C:16]([NH:21][C:22](=[O:33])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:31])([F:30])[F:32])[CH:24]=2)=[CH:15][C:14]=1[C:3]1[C:2](=[O:35])[NH:13][C:6]2[N:7]=[C:8]([S:11][CH3:12])[N:9]=[CH:10][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 59833857HCID 59833857, compound

Product 1

HCID 59833795HCID 59833795, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of N-[3-(7-amino-2-methylsulfanyl-pyrido[2,3-d]pyrimidin-6-yl)-4-chloro-phenyl]-3-trifluoromethyl-benzamide (1.0 g, 2.04 mmol) in TFA (10 mL) is slowly added NaNO2 (423 mg, 6.12 mmol) at 0° C. with stirring for 20 minutes. The solvents are evaporated, diluted with EtOAc and washed with saturated K2CO3, brine and water. The organic layer is dried, filtered and concentrated to give crude product, which is purified by flash silica gel column, eluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH(NH3, 2N)(93/7%), to give the title intermediate as a solid (0.644 g, 64.4%).

Workup

  1. customat 0° C.
  2. customThe solvents are evaporated
  3. additiondiluted with EtOAc
  4. washwashed with saturated K2CO3, brine and water
  5. customThe organic layer is dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give crude product, which
  9. customis purified by flash silica gel column
  10. washeluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH(NH3, 2N)(93/7%)

Sources & evidence

ORD record
ord-8777632244e74e899c0a9bf39260cbb7
Source dataset
uspto-grants-2008_11
Patent number
US07449582B2

Reaction notes

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