Ammonium formate → 1-(3-Methyl-isoquinolin-5-yl)-3-pyrrolidin-3-yl urea

HRID 490289Notes

Reaction equation

HRID 490289 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]([NH:16][C:17]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:18]=2[CH:19]=[C:20]([CH3:27])[N:21]=[CH:22]3)=[O:15])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO.ClCCl>[CH3:27][C:20]1[N:21]=[CH:22][C:23]2[C:18]([CH:19]=1)=[C:17]([NH:16][C:14]([NH:13][CH:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)=[O:15])[CH:26]=[CH:25][CH:24]=2

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 104286221-(1-Benzyl-pyrrolidin-3-yl)-3-(3-methyl-isoquinolin-5-yl)urea

Product 1

HCID 688557451-(3-Methyl-isoquinolin-5-yl)-3-pyrrolidin-3-yl ureaYield 69.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (D3) (2.30 g, 6.40 mmol), ammonium formate (2.02 g, 32.10 mmol) and 10% palladium on carbon (1 g) in methanol (100 mL) was heated at 70° C. for 3 h, then cooled to 25° C. and filtered through Celite. Evaporation in vacuo gave an oil which was suspended in dichloromethane and washed with saturated sodium carbonate solution. The organic layer was removed, dried (Na2SO4), and the solvents evaporated in vacuo to give the title compound as a yellow oil (1.2 g). 1H NMR (CDCl3) δ: 2.05-2.20 (2H, m), 2.68 (3H, s), 2.85-2.95 (2H, m), 3.00-3.15 (2H, m), 4.35-4.45 (1H, m), 5.85-5.90 (1H, m), 7.40-7.50 (2H, m), 7.62 (1H, s), 7.72 (1H, d, J=8.2 Hz), 7.91 (1H, d, J=7.6 Hz), 9.14 (1H, s).

Workup

  1. filtrationfiltered through Celite
  2. customEvaporation in vacuo
  3. customgave an oil which
  4. washwashed with saturated sodium carbonate solution
  5. customThe organic layer was removed
  6. dry with materialdried (Na2SO4)
  7. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-2e7d56c0bcf74146a804d5c5f54f7776
Source dataset
uspto-grants-2009_05
Patent number
US07528150B2

Reaction notes

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