Morpholine → HCID 18548758, compound

HRID 1266896Notes

Reaction equation

HRID 1266896 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.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>CCO.O>[N:31]1([CH2:2][C:3]2[N:4]=[C:5]([C:8]3[CH:9]=[C:10]([C:14]4[CH2:20][C:19](=[O:21])[NH:18][C:17]5[CH:22]=[C:23]([N:26]6[CH:30]=[CH:29][CH:28]=[CH:27]6)[CH:24]=[CH:25][C:16]=5[N:15]=4)[CH:11]=[CH:12][CH:13]=3)[O:6][CH:7]=2)[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 18548707HCID 18548707, compound

Product 1

HCID 18548758HCID 18548758, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

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), morpholine (0.25 mL) and KI (5 mg) in EtOH (1 mL) was stirred at 60° C. for 2 h. in H2O (20 mL) was added to the cooled solution 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 subsequently isolated by filtration to give the title compound (60 mg) as yellow solid.

Workup

  1. additionwas added to the cooled solution
  2. filtrationthe precipitate was collected by filtration
  3. custompurified by chromatography on silica gel
  4. additionbeing set to 11 by addition of 1N NaOH solution
  5. customthe solid was subsequently isolated by filtration

Sources & evidence

ORD record
ord-d4c4320703934d44a2c0bba133b19392
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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