Acetic Acid → HCID 89726588, compound

HRID 1777746Notes

Reaction equation

HRID 1777746 reaction equation
[CH2:1]([O:8][C:9](=[O:20])[CH2:10][N:11]1[C:19]2[CH2:18][CH2:17][NH:16][CH2:15][C:14]=2[N:13]=[CH:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[BH3-][C:24]#N.[Na+].CC(O)=O>CO.C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:20])[CH2:10][N:11]1[C:19]2[CH2:18][CH2:17][N:16]([CH3:24])[CH2:15][C:14]=2[N:13]=[CH:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 89726280HCID 89726280, compound

Product 1

HCID 89726588HCID 89726588, compoundYield 29.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-1-yl)-acetic acid benzyl ester (176 mg) in MeOH was added formaldehyde (36.5% in water, 0.052 mL) followed by NaBH3CN (29 mg) and AcOH (0.5 mL). The reaction mixture was stirred at RT overnight. DCM was added and the mixture was washed with sat. NaHCO3. The aq. layer was extracted with DCM, the combined org. layers were dried (MgSO4), filtered off and evaporated to dryness. The residue was purified by CC (Biotage, SNAP 10 g cartridge, solvent A: DCM; solvent B: DCM/MeOH 8/2; gradient in % B: 25 for 3CV, 25 to 50 over 2CV, 50 for 5CV, 50 to 100 over 3CV, 100 for 2CV) to afford (5-methyl-4,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-1-yl)-acetic acid benzyl ester (39 mg, yellow oil). LC-MS (B): tR=0.46 min; [M+H]+: 286.16.

Workup

  1. washthe mixture was washed with sat. NaHCO3
  2. extractionThe aq. layer was extracted with DCM
  3. dry with materiallayers were dried (MgSO4)
  4. filtrationfiltered off
  5. customevaporated to dryness
  6. customThe residue was purified by CC (Biotage, SNAP 10 g cartridge, solvent A: DCM; solvent B: DCM/MeOH 8/2; gradient in % B: 25 for 3CV, 25 to 50 over 2CV, 50 for 5CV, 50 to 100 over 3CV, 100 for 2CV)

Sources & evidence

ORD record
ord-cba2136f208d423395a0a3e7c04733c3
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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