Acetic Acid → HCID 11603458, compound

HRID 548975Notes

Reaction equation

HRID 548975 reaction equation
[N+](C1C=CC([C:10]2[C:15]3[C:16]4[C:22]([C:23]([O-:25])=O)=[CH:21][CH:20]=[C:19]([O:26][CH3:27])[C:17]=4[O:18][C:14]=3[CH:13]=[CH:12][N:11]=2)=CC=1)([O-])=O.[NH2:28][C:29]1[C:34]([Cl:35])=[CH:33][N:32]=[CH:31][C:30]=1[Cl:36].[H-].[Na+].C(O)(=O)C>CN(C=O)C.O>[Cl:36][C:30]1[CH:31]=[N:32][CH:33]=[C:34]([Cl:35])[C:29]=1[NH:28][C:23]([C:22]1[C:16]2[C:15]3[CH:10]=[N:11][CH:12]=[CH:13][C:14]=3[O:18][C:17]=2[C:19]([O:26][CH3:27])=[CH:20][CH:21]=1)=[O:25]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 66592634HCID 66592634, compound

Product 1

HCID 11603458HCID 11603458, compoundYield 46.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a well stirred solution of 4-nitrophenyl-6-methoxybenzo[4,5]furo[3,2-c]pyridine-9-carboxylate (from step 14) (55 mg, 0.15 mmol) and 4-amino-3,5-dichloropyridine (50 mg, 0.30 mmol) in DMF (2.0 mL) was added sodium hydride (60% dispersion in mineral oil) (18 mg, 0.45 mmol) at −5° C. and stirred for 3040 minutes. Excess of DMF was removed under reduce pressure, the residue obtained was diluted with water (5 mL) and acidified to pH 5-6 with acetic acid. The solid obtained was filtered, washed with water and dried to afford product (27 mg) as off-white solid.

Workup

  1. customExcess of DMF was removed
  2. customthe residue obtained
  3. customThe solid obtained
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ef61f0e8363846048f368395d61d81e8
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Reaction notes

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