Acetic Acid → HCID 58938661, compound

HRID 598147Notes

Reaction equation

HRID 598147 reaction equation
[NH2:1][C:2]1[C:3]2[CH:11]=[CH:10][N:9]([C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])[C:4]=2[C:5](=[O:8])[NH:6][N:7]=1.[CH:21](=O)[CH2:22][CH3:23].CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[C:17]1([CH3:18])[CH:16]=[C:15]([CH3:19])[CH:14]=[C:13]([CH3:20])[C:12]=1[N:9]1[C:4]2[C:5](=[O:8])[NH:6][N:7]=[C:2]([NH:1][CH2:21][CH2:22][CH3:23])[C:3]=2[CH:11]=[CH:10]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 67266806HCID 67266806, compound

Product 1

HCID 58938661HCID 58938661, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-amino-1-mesityl-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-one (50 mg, 0.19 mmol), propionaldehyde (0.034 ml, 0.47 mmol), AcOH (0.013 ml, 0.224 mmol) and dichloromethane (10 ml) was stirred for 30 min before addition of NaBH(OAc)3 (99 mg, 0-47 mmol). The mixture was stirred for 3 hours, then washed with saturated sodium bicarbonate (20 ml), dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate (1:1-1:2) to give 19.4 mg (34%) of the title compound as crystals.

Workup

  1. washwashed with saturated sodium bicarbonate (20 ml)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with hexane/ethyl acetate (1:1-1:2)

Sources & evidence

ORD record
ord-36a01590738a4c6f896b10f2868cea2b
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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