1-Hydroxybenzotriazole hydrate → 1,1-dimethylethyl 2-[4-(aminocarbonyl)-5-propyl-1H-imidazol-2-yl]-2,3-dihydro-1H-indole-1-carboxylate

HRID 551413Notes

Reaction equation

HRID 551413 reaction equation
O.O[N:3]1C2C=CC=CC=2N=N1.[C:12]([C:15]1[N:16]=[C:17]([CH:23]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]2[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[NH:18][C:19]=1[CH2:20][CH2:21][CH3:22])(O)=[O:13]>C(Cl)Cl>[NH2:3][C:12]([C:15]1[N:16]=[C:17]([CH:23]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]2[C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[NH:18][C:19]=1[CH2:20][CH2:21][CH3:22])=[O:13]

Participants

4

Reactant 2

HCID 27960291-Hydroxybenzotriazole hydrateHCID 219140991,1-dimethylethyl 2-(4-carboxy-5-propyl-1H-imidazol-2-yl)-2,3-dihydro-1H-indole-1-carboxylate

Product 1

HCID 219141071,1-dimethylethyl 2-[4-(aminocarbonyl)-5-propyl-1H-imidazol-2-yl]-2,3-dihydro-1H-indole-1-carboxylateYield 35.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Hydroxybenzotriazole hydrate (0.00318 mole) was added to a solution of compound 105 (0.00159 mole) in DCM (160 mL) at room temperature. N,N′-methane-tetrayl-biscyclohexanamine (0.00206 mole) was added neat at room temperature. After 60 minutes, NH3 gas was bubbled in for 5 minutes, and a solid precipitated out. The mixture was allowed to sit over the weekend. The mixture was filtered, and the filtrate was extracted with saturated NaHCO3. The organic phases were dried over MgSO4, filtered, and concentrated. The residue was purified by liquid chromatography, yielding 0.21 g of 1,1-dimethylethyl 2-[4-(aminocarbonyl)-5-propyl-1H-imidazol-2-yl]-2,3-dihydro-1H-indole-1-carboxylate (compound 106).

Workup

  1. customNH3 gas was bubbled in for 5 minutes
  2. customa solid precipitated out
  3. filtrationThe mixture was filtered
  4. extractionthe filtrate was extracted with saturated NaHCO3
  5. dry with materialThe organic phases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by liquid chromatography

Sources & evidence

ORD record
ord-db5d38233fd743f18cc637a153034d51
Source dataset
uspto-grants-2011_05
Patent number
US07947713B2

Reaction notes

Loading…