Cyclopropanemethanamine → HCID 67456561, compound

HRID 639688Notes

Reaction equation

HRID 639688 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[N:28]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:27](=[O:36])[NH:26][C:7]=2[C:8]([N:11]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:9][CH:10]=1)=O.[NH2:37][CH2:38][CH:39]1[CH2:41][CH2:40]1>>[CH:39]1([CH2:38][NH:37][C:3]([C:5]2[C:6]3[N:28]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:27](=[O:36])[NH:26][C:7]=3[C:8]([N:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[N:9][CH:10]=2)=[O:2])[CH2:41][CH2:40]1

Participants

3

Reactant 2

HCID 75646CyclopropanemethanamineHCID 67456184HCID 67456184, compound

Product 1

HCID 67456561HCID 67456561, compound

Conditions

Temperature
120 °C

Procedure

1-benzyl-4-dibenzylamino-2-oxo-2,3-dihydro-1H-imidazo[4,5,c]pyridine-7-carboxylic acid methyl ester (50 mg, 0.1 mmol) was suspended in 2 mL of (aminomehtyl) cyclopropane and the mixture was stirred at 120° C. overnight. The excess of amine was removed in vacuo and the gum was partitioned in water (20 mL) and ethyl acetate (50 mL), the organic layer was isolated, dried over MgSO4 and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel using 5% of methanol in dichloromethane to give 10 mg of the title compound as a yellow gum.

Workup

  1. customThe excess of amine was removed in vacuo
  2. customthe gum was partitioned in water (20 mL)
  3. customethyl acetate (50 mL), the organic layer was isolated
  4. dry with materialdried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel using 5% of methanol in dichloromethane

Sources & evidence

ORD record
ord-91508a2131cc493ca7dd80ae99a96829
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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