Water → HCID 57445001, compound

HRID 1645253Notes

Reaction equation

HRID 1645253 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=2)[NH2:11])[CH2:3][CH2:2]1.C(Cl)(=O)O[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.NC1C=CC([NH:35][C:36](=O)[O:37]C(C)(C)C)=CC=1.O>C1COCC1>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][C:8]2[CH:9]=[C:10]([NH:11][C:36]([NH:35][C:17]3[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=3)=[O:37])[CH:12]=[CH:13][CH:14]=2)[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 821294-Nitrophenyl chloroformateHCID 688611tert-Butyl (4-aminophenyl)carbamateHCID 10964063-(Morpholin-4-ylmethyl)aniline

Product 1

HCID 57445001HCID 57445001, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(morpholinomethyl)aniline (0.46 g), TEA (0.37 mL) and 4-nitrophenyl carbonochloridate (530 mg) in THF (18 mL) was stirred at ambient temperature for 2 hours, treated with tert-butyl 4-aminophenylcarbamate (500 mg) and an additional 0.37 mL of TEA. the resulting mixture was stirred at ambient temperature for 48 hours, poured into water and extracted 3× with ethyl acetate. The extract was washed with brine, dried (MgSO4), filtered and concentrated. The concentrate was purified by flash chromatography on silica gel with 2% methanol/dichloromethane to provide 1-(3-(morpholinomethyl)phenyl)-3-(4-nitrophenyl)urea which was dissolved in dichloromethane (30 mL), cooled in an ice bath, and treated with TFA (1.8 mL). The reaction mixture was stirred for 30 minutes at 0° C. and for 12 hours at ambient temperature, and concentrated three times from methanol/toluene.

Workup

  1. extractionextracted 3× with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash chromatography on silica gel with 2% methanol/dichloromethane

Sources & evidence

ORD record
ord-5ceae91cfe4c49b9abbbf2ed52aa1c7d
Source dataset
uspto-grants-2012_02
Patent number
US08124759B2

Reaction notes

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