Formaldehyde → HCID 178461560, compound

HRID 1830029Notes

Reaction equation

HRID 1830029 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:9]=[CH:10][C:11]2[NH:15][C:14]([C:16]3[C:24]4[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=4)[NH:18][N:17]=3)=[N:13][C:12]=2[CH:26]=1.C=O.[BH3-][C:30]#N.[Na+]>CO.C(O)(=O)C>[CH3:1][C@H:2]1[CH2:7][N:6]([CH3:30])[CH2:5][CH2:4][N:3]1[C:8]1[CH:9]=[CH:10][C:11]2[NH:15][C:14]([C:16]3[C:24]4[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=4)[NH:18][N:17]=3)=[N:13][C:12]=2[CH:26]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178461561HCID 178461561, compound

Product 1

HCID 178461560HCID 178461560, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

3-[6-((2S)-2-methylpiperazinyl)benzimidazol-2-yl]-6-chloro-1H-indazole (1 equivalent) is dissolved in a mixture of MeOH and acetic acid (10: 1), on molecular sieves. Paraformaldehyde (10 equivalents) is added in one portion. The reaction mixture is stirred at room temperature overnight then solid NaCNBH3 is added in small portions. The reaction mixture is refluxed for 5 hours, cooled to room temperature, filtered, and concentrated under reduced pressure. The residue is dissolved in dichloromethane and washed with saturated aqueous NaHCO3. The organic solution is dried over Na2SO4, and the solvent removed under reduced pressure to afford the desired product.

Workup

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue is dissolved in dichloromethane
  6. washwashed with saturated aqueous NaHCO3
  7. dry with materialThe organic solution is dried over Na2SO4
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-debbb8e85be64ff8b406dca7a9899c26
Source dataset
uspto-grants-2006_06
Patent number
US07064215B2

Reaction notes

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