Acetic Acid → tert-Butyl {2-[(5-carbamoyl-1H-imidazol-4-yl)amino]ethyl}carbamate

HRID 912719Notes

Reaction equation

HRID 912719 reaction equation
Cl.[NH2:2][C:3]1[NH:7][CH:6]=[N:5][C:4]=1[C:8]([NH2:10])=[O:9].C(N(CC)CC)C.C(O)(=O)C.[C:22]([NH:29][CH2:30][CH:31]=O)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO>[C:8]([C:4]1[NH:5][CH:6]=[N:7][C:3]=1[NH:2][CH2:31][CH2:30][NH:29][C:22](=[O:23])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])(=[O:9])[NH2:10]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5003444Sodium cyanoborohydrideHCID 178479549HCID 178479549, compound

Product 1

HCID 86631143tert-Butyl {2-[(5-carbamoyl-1H-imidazol-4-yl)amino]ethyl}carbamateYield 55.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The reaction mixture of 5-amino-imidazole-4-carboxamide hydrochloride (10 g, 62 mmol) and triethylamine (8.7 mL, 63 mmol) in anhydrous methanol (100 mL) was stirred for 15 min. Acetic acid (0.9 mL, 16 mmol) and N-boc-2-aminoacetaldehyde (11 g, 67 mmol) were added. The reaction mixture was stirred for 3 h, then sodium cyanoborohydride (5 g, 80 mmol) was added and the mixture was stirred o.n. A solution of saturated sodium bicarbonate was added and most of the methanol was removed in vacuo. The mixture was extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated. Purification by silica gel column chromatography, (dichloromethane/ammonia (7N in methanol), 0-6%) gave 9.2 g (55% yield) of the title compound.

Workup

  1. stirringThe reaction mixture was stirred for 3 h
  2. stirringthe mixture was stirred o.n
  3. customwas removed in vacuo
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. concentrationconcentrated
  7. customPurification by silica gel column chromatography, (dichloromethane/ammonia (7N in methanol), 0-6%)

Sources & evidence

ORD record
ord-d10587cb67d94995b38a212b3516c023
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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