Formaldehyde → HCID 71478936, compound

HRID 64463Notes

Reaction equation

HRID 64463 reaction equation
Cl.Cl.[CH:3]1([CH2:9][O:10][C:11]2[C:12]3[N:13]([C:17]([C:21]([NH:23][C@H:24]4[CH2:28][CH2:27][NH:26][CH2:25]4)=[O:22])=[C:18]([CH3:20])[N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C=O.[C:31](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClC(Cl)C.C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH:3]1([CH2:9][O:10][C:11]2[C:12]3[N:13]([C:17]([C:21]([NH:23][C@H:24]4[CH2:28][CH2:27][N:26]([CH3:31])[CH2:25]4)=[O:22])=[C:18]([CH3:20])[N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 867134828-(cyclohexylmethoxy)-2-methyl-N-[(3S)-pyrrolidin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride

Product 1

HCID 71478936HCID 71478936, compoundYield 72.1%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 63651,1-DichloroethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of 400 mg of 8-(cyclohexylmethoxy)-2-methyl-N-[(3S)-pyrrolidin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride, 0.26 ml of triethylamine, and 0.23 ml of a 37% aqueous formaldehyde solution in 11 ml of dichloroethane was added 592 mg of sodium triacetoxyborohydride under ice-cooling, followed by stirring at room temperature for 1 hour. To the reaction mixture were added a saturated aqueous sodium hydrogen carbonate solution and chloroform to carry out a layer separation operation. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 249 mg of 8-(cyclohexylmethoxy)-2-methyl-N-[(3S)-1-methylpyrrolidin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide.

Workup

  1. temperaturecooling
  2. customa layer separation operation
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-85557d72e1444ca1ac1a59db39a59864
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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