Dimethylamine → HCID 18548729, compound

HRID 1266895Notes

Reaction equation

HRID 1266895 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:9]=[C:10]([C:14]3[CH2:20][C:19](=[O:21])[NH:18][C:17]4[CH:22]=[C:23]([N:26]5[CH:30]=[CH:29][CH:28]=[CH:27]5)[CH:24]=[CH:25][C:16]=4[N:15]=3)[CH:11]=[CH:12][CH:13]=2)[O:6][CH:7]=1.[CH3:31][NH:32][CH3:33].O>CCO>[CH3:31][N:32]([CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:9]=[C:10]([C:14]3[CH2:20][C:19](=[O:21])[NH:18][C:17]4[CH:22]=[C:23]([N:26]5[CH:30]=[CH:29][CH:28]=[CH:27]5)[CH:24]=[CH:25][C:16]=4[N:15]=3)[CH:11]=[CH:12][CH:13]=2)[O:6][CH:7]=1)[CH3:33]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 18548707HCID 18548707, compound

Product 1

HCID 18548729HCID 18548729, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 4-[3-(4-chloromethyl-oxazol-2-yl)-phenyl]-8-pyrrol-1-yl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 78a) (125 mg) and KI (5 mg) in a 5.6M solution of dimethylamine in EtOH (1.5 mL) was stirred at 20° C. for 16 h. H2O (20 mL) was added and the precipitate was collected by filtration and purified by chromatography on silica gel using MeOH as eluent. The product was stirred with 20% aqueous MeOH (10 mL) the pH of the mixture being set to 11 by addition of 1N NaOH solution, and the solid was isolated by filtration to give the title compound (50 mg) as yellow solid.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. custompurified by chromatography on silica gel
  3. stirringThe product was stirred with 20% aqueous MeOH (10 mL) the pH of the mixture
  4. additionbeing set to 11 by addition of 1N NaOH solution
  5. customthe solid was isolated by filtration

Sources & evidence

ORD record
ord-b4e4f1faf25443efba03dd0cad53d7b6
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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