Potassium Carbonate → 7-Chloro-5-methyl-2-(2-(1-methyl-1H-benzo[D]imidazol-2-YL)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-C]pyridine-1,6(5H)-dione

HRID 1752604Notes

Reaction equation

HRID 1752604 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl.Cl.[CH3:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[CH2:19][CH2:20][NH2:21].[CH3:22][N:23]1[CH:28]=[C:27]([CH2:29]Cl)[C:26]([C:31](OC)=[O:32])=[C:25]([Cl:35])[C:24]1=[O:36]>CO.CC#N>[Cl:35][C:25]1[C:24](=[O:36])[N:23]([CH3:22])[CH:28]=[C:27]2[CH2:29][N:21]([CH2:20][CH2:19][C:11]3[N:10]([CH3:9])[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[N:12]=3)[C:31](=[O:32])[C:26]=12

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 450751602-(1-methyl-1H-1,3-benzodiazol-2-yl)ethan-1-amine dihydrochlorideHCID 904216921-Methyl-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-5-chloromethyl-pyridine2×

Product 1

HCID 717435967-Chloro-5-methyl-2-(2-(1-methyl-1H-benzo[D]imidazol-2-YL)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-C]pyridine-1,6(5H)-dioneYield 54.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

K2CO3 (8.35 g, 60.4 mmol) was added rapidly to a suspension of 2-(1-methyl-1H-benzo[d]imidazol-2-yl)ethanamine dihydrochloride (5 g, 20.15 mmol) in MeOH (50 ml) and the reaction was stirred for about 5 h. The mixture was filtered and the filtrate was concentrated. The residue and TEA (28.1 ml, 201 mmol) were added to a solution of 1-methyl-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-5-chloromethyl-pyridine (5.04 g, 20.15 mmol, see compound (6) of Example b1)) in MeCN (100 ml). The mixture was heated at about 90° C. overnight. The reaction was cooled to r.t. and the mixture was filtered through a sintered glass funnel. The solid was washed with water and dried to afford the title compound (3.9 g, 10.93 mmol, 54.2% yield).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. temperatureThe reaction was cooled to r.t.
  4. filtrationthe mixture was filtered through a sintered glass funnel
  5. washThe solid was washed with water
  6. customdried

Sources & evidence

ORD record
ord-6fec628c8c324258a710ad9ffe818fa3
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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