5,6-bis(Benzyloxy)-N-(cyclopropylmethyl)-N-methylpyridazin-3-amine → HCID 178482567, compound

HRID 927156Notes

Reaction equation

HRID 927156 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([N:23]([CH2:25][CH:26]2[CH2:28][CH2:27]2)[CH3:24])[N:12]=[N:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[CH:26]1([CH2:25][N:23]([CH3:24])[C:11]2[CH:10]=[C:9]([OH:8])[C:14](=[O:15])[NH:13][N:12]=2)[CH2:27][CH2:28]1

Participants

4

Reactant 1

HCID 712705445,6-bis(Benzyloxy)-N-(cyclopropylmethyl)-N-methylpyridazin-3-amine2×

Product 1

HCID 178482567HCID 178482567, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 5,6-bis(benzyloxy)-N-(cyclopropylmethyl)-N-methylpyridazin-3-amine (Intermediate 46; 2.44 mmol) and palladium on carbon (10% wt loading, dry basis; 0.259 g, 0.244 mmol) in ethyl acetate (10 ml) was stirred under a hydrogen atmosphere for 2 hours. The reaction mixture was filtered through a diatomaceous earth cartridge commercially sold under the trade mark ‘Celite’, eluting with ethyl acetate, tetrahydrofuran and methanol. The filtrate was concentrated in vacuo to afford a brown solid, which was triturated from ethyl acetate to give the title compound as a pale brown solid (27.9 mg, 38%).

Workup

  1. filtrationThe reaction mixture was filtered through a diatomaceous earth cartridge
  2. washeluting with ethyl acetate, tetrahydrofuran and methanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto afford a brown solid, which
  5. customwas triturated from ethyl acetate

Sources & evidence

ORD record
ord-9ec915b912264ce29b9059138d817b1c
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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