Water → HCID 18548815, compound

HRID 1266894Notes

Reaction equation

HRID 1266894 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.[I-].[K+].[CH3:33][NH2:34].O>C(O)C>[CH3:33][NH:34][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

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 6329MethylamineHCID 18548707HCID 18548707, compound

Product 1

HCID 18548815HCID 18548815, 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 potassium iodide (5 mg) in a 8M solution of methylamine in ethanol (1.5 mL) was stirred at 20° C. for 16 h. H2O (20 mL) was added and the precipitated 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 (54 mg) as yellow solid.

Workup

  1. filtrationthe precipitated 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-97834fb7a1dc4366b45c7c102231005d
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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