1,2-Dichloroethane → HCID 89691180, compound

HRID 1054199Notes

Reaction equation

HRID 1054199 reaction equation
[CH:1]([C:3]1[CH:4]=[N:5][NH:6][C:7]=1[C:8]([OH:10])=[O:9])=O.[N:11]1[C:20]2[C:15](=[CH:16][C:17]([NH2:21])=[CH:18][CH:19]=2)[N:14]=[CH:13][CH:12]=1.ClCCCl.[BH4-].[Na+]>C(O)(=O)C.C(OCC)(=O)C.CO.CN(C=O)C>[N:11]1[C:20]2[C:15](=[CH:16][C:17]([NH:21][CH2:1][C:3]3[CH:4]=[N:5][NH:6][C:7]=3[C:8]([OH:10])=[O:9])=[CH:18][CH:19]=2)[N:14]=[CH:13][CH:12]=1

Participants

9

Reactant 4

HCID 111,2-DichloroethaneHCID 2378596-QuinoxalinamineHCID 4311764Sodium borohydrideHCID 224781464-Formyl-1H-pyrazole-5-carboxylic acid

Product 1

HCID 89691180HCID 89691180, compoundYield 104.6%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of product (4-B) (100 mg, 0.71 mmol) and quinoxalin-6-amine (104 mg, 0.71 mmol) in a solution of 1,2-dichloroethane (DCE, 5 mL) and DMF (5 mL) was added acetic acid (5 drops) at rt. The reaction mixture was then stirred for 16 h. MeOH (5 mL) was added, followed by NaBH4 (100 mg, 2.63 mmol). The reaction mixture was stirred at rt for another 30 min. The solution was diluted with ethyl acetate (30 mL); washed with 5% citric acid (10 mL) and brine (20 mL); dried over Na2SO4; and concentrated to give crude product (5-B) (200 mg, 99%) as a yellow solid. LC-MS (M+H)+=270.

Workup

  1. stirringThe reaction mixture was stirred at rt for another 30 min
  2. washwashed with 5% citric acid (10 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationand concentrated

Sources & evidence

ORD record
ord-9ff9f149921e4294a3b5cea6e5e5e7a0
Source dataset
uspto-grants-2016_07
Patent number
US09394296B2

Reaction notes

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