Formaldehyde → HCID 22937007, compound

HRID 1433745Notes

Reaction equation

HRID 1433745 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH2:22][CH:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)=[C:16]([C:19]#[N:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:29][C:30]([NH:32][CH3:33])=[O:31].C=O.[C:36]([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.CO.C(OCC)(=O)C.O.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH2:22][CH:23]4[CH2:24][CH2:25][N:26]([CH3:36])[CH2:27][CH2:28]4)=[C:16]([C:19]#[N:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:29][C:30]([NH:32][CH3:33])=[O:31]

Participants

10

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 22936501HCID 22936501, compound

Product 1

HCID 22937007HCID 22937007, compoundYield 64.7%

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving N-(2-chloro-4-((6-cyano-7-(4-piperidylmethoxy)-4-quinolyl)oxy)phenyl)-N′-methylurea (15 mg) in tetrahydrofuran (0.5 ml) and methanol (0.5 ml), there were added 37% aqueous formaldehyde (0.03 ml), acetic acid (0.06 ml) and sodium cyanoborohydride (5.0 mg) at room temperature, and the mixture was stirred for 1 hour. Water was added to the reaction solution, saturated aqueous sodium bicarbonate was added for neutralization, and extraction was performed with ethyl acetate. The organic layer was washed with water and the solvent was distilled off to obtain a crude product. This was recrystallized with ethyl acetate to obtain the title compound (10 mg) as white crystals.

Workup

  1. additionwas added for neutralization, and extraction
  2. washThe organic layer was washed with water
  3. distillationthe solvent was distilled off
  4. customto obtain a crude product
  5. customThis was recrystallized with ethyl acetate

Sources & evidence

ORD record
ord-51cb4b2747cc4d46959c4eb8ce251b36
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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