Potassium Carbonate → HCID 59843091, compound

HRID 1878772Notes

Reaction equation

HRID 1878772 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][CH2:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:28]=[CH:27][C:26](=[O:29])[N:25]([CH2:30][CH2:31][O:32][C:33]3[C:42]4[C:37](=[CH:38][C:39]([O:45][CH3:46])=[C:40]([CH:43]=[O:44])[CH:41]=4)[N:36]=[CH:35][CH:34]=3)[N:24]=2)[CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl.CO>[NH2:15][CH2:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:28]=[CH:27][C:26](=[O:29])[N:25]([CH2:30][CH2:31][O:32][C:33]3[C:42]4[C:37](=[CH:38][C:39]([O:45][CH3:46])=[C:40]([CH2:43][OH:44])[CH:41]=4)[N:36]=[CH:35][CH:34]=3)[N:24]=2)[CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86624660HCID 86624660, compound

Product 1

HCID 59843091HCID 59843091, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Sodium triacetoxyborohydride (200 mg, 944 μmol) was added to a mixture of 4-(2-(3-(3-(aminomethyl)phenyl)-6-oxopyridazin-1(6H)-yl)ethoxy)-7-methoxyquinoline-6-carbaldehyde (16 mg, 37 μmol) in CHCl3 (3 mL) and MeOH (1 mL) were added (to keep solvent volume). After 19 h, K2CO3 (500 mg) was added. After 3 h, the mixture was filtered and concentrated. The residue was purified on silica (5% (2 N NH3-MeOH) in CH2Cl2 to give a film (10 mg, 62%). LCMS (ESI pos. ion): calc'd for C24H24N4O4: 432.2; found 433.2 (M+1).

Workup

  1. additionwere added (to keep solvent volume)
  2. waitAfter 3 h
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated
  5. customThe residue was purified on silica (5% (2 N NH3-MeOH) in CH2Cl2
  6. customto give a film (10 mg, 62%)

Sources & evidence

ORD record
ord-d834be8bfe3c462e9cfb80f9bbf49c7e
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

Loading…