Benzaldehyde → HCID 18789581, compound

HRID 1106814Notes

Reaction equation

HRID 1106814 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:21])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]([NH2:19])=[O:18])=[CH:13][CH:12]=1)[CH2:9][CH3:10].[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([BH3-])#N.[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]([NH2:19])=[O:18])=[CH:13][CH:12]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 22675565HCID 22675565, compound

Product 1

HCID 18789581HCID 18789581, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 6-[N-(5-bromo-2-aminobenzyl)-N-ethylamino]pyridazine-3-carboxamide (900 mg, 2.57 mmol), benzaldehyde (0.6 ml, 5.9 mmol) and methanol (50 ml) stirred at 50° C., was added portionwise sodium cyanoborohydride (400 mg, 6.36 mmol). The solution was stirred for 16 hours at 20° C., by which time the product crystallised. It was filtered off and washed with methanol (10 ml) to give 6-[N-(5-bromo-2-benzylaminobenzyl)-N-ethylamino]pyridazine-3-carboxamide (850 mg) m.p. 160-162° C.

Workup

  1. stirringThe solution was stirred for 16 hours at 20° C., by which time the product
  2. customcrystallised
  3. filtrationIt was filtered off
  4. washwashed with methanol (10 ml)

Sources & evidence

ORD record
ord-4f09a66c372b4a018414bf55ff677c22
Source dataset
uspto-grants-2000_05
Patent number
US06057345

Reaction notes

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