Ammonia → Benzyl 2-[({[(4-chlorophenyl)amino]carbonyl}amino)methyl]morpholine-4-carboxylate

HRID 1371380Notes

Reaction equation

HRID 1371380 reaction equation
[NH2:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:4]1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[O:28])=[CH:22][CH:21]=1.ClCCl.C(O)C.N>ClCCl.CO>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:1][CH2:2][CH:3]2[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])[CH2:4]2)=[O:28])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 76934-Chlorophenyl IsocyanateHCID 15549650Benzyl 2-(aminomethyl)morpholine-4-carboxylateHCID 21584144Dichloromethane ethanol

Product 1

HCID 21070806Benzyl 2-[({[(4-chlorophenyl)amino]carbonyl}amino)methyl]morpholine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Intermediate 5 (2.0 g) in dichloromethane (100 ml) was added 4-chlorophenylisocyanate (1.35 g). The mixture was stirred at 22° C. for 18 h before 10% 0.880 ammonia solution in methanol (10 ml) was added. Stirring was continued for a further 30 min before the solvent was removed in vacuo. The residue was purified by Biotage flash chromatography on silica gel, eluting with 33% ethyl acetate/cyclohexane; further purification by Biotage flash chromatography on silica gel, eluting with 500:8:1 dichloromethane/ethanol/0.880 ammonia solution gave the impure title compound as a buff solid (3.6 g).

Workup

  1. additionwas added
  2. customwas removed in vacuo
  3. customThe residue was purified by Biotage flash chromatography on silica gel
  4. washeluting with 33% ethyl acetate/cyclohexane
  5. customfurther purification by Biotage flash chromatography on silica gel
  6. washeluting with 500:8:1 dichloromethane/ethanol/0.880 ammonia solution

Sources & evidence

ORD record
ord-a1726670756144ff9d197d6c5f91a4a7
Source dataset
uspto-grants-2007_01
Patent number
US07157457B2

Reaction notes

Loading…