Ammonia → Tert-butyl 4-(4-carbamoyl-2-oxo-2,3-dihydroimidazol-1-yl)piperidine-1-carboxylate

HRID 1867604Notes

Reaction equation

HRID 1867604 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([C:19]([OH:21])=O)[NH:16][C:15]2=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C[N:25](C)CCCN=C=NCC.O.N1(O)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.N.C(=O)(O)[O-].[Na+]>CN(C)C=O.ClCCl>[NH2:25][C:19]([C:17]1[NH:16][C:15](=[O:22])[N:14]([CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:9][CH2:10]2)[CH:18]=1)=[O:21]

Participants

9

Reactant 6

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59006370HCID 59006370, compound

Product 1

HCID 59006367Tert-butyl 4-(4-carbamoyl-2-oxo-2,3-dihydroimidazol-1-yl)piperidine-1-carboxylateYield 37.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-[1-(tert-butoxycarbonyl)piperidin-4-yl]-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid (210 mg, 0.675 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (388 mg, 2.02 mmol), 1H-1,2,3-benzotriazol-1-ol hydrate (273 mg, 2.02 mmol), N,N-diisopropylethylamine (0.352 mL, 2.02 mmol), and ammonia (0.5 M, 2.02 mmol, 4.05 mL) were stirred at room temperature in dimethylformamide (10 mL). After 3 h, the reaction was worked up with dichloromethane and saturated sodium bicarbonate. The organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→15% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound (78 mg). MS 255.2 (M+1-tert butyl)

Workup

  1. washThe organic extracts were washed with brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (100% dichloromethane→15% methanol {1% ammonium hydroxide}/dichloromethane)

Sources & evidence

ORD record
ord-d0099aa00efa4223bb8d44b767a8e95c
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

Loading…