Tert-butyl 3-(2-amino-4-methylphenylcarbamoyl)azetidine-1-carboxylate → HCID 178423469, compound

HRID 1842487Notes

Reaction equation

HRID 1842487 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([CH:12]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]1)=O.NC1C=CC(C)=CC=1NC(C1CN(C(OC(C)(C)C)=O)C1)=O>CC(O)=O>[CH3:8][C:6]1[CH:5]=[CH:4][C:3]2[NH:9][C:10]([CH:12]3[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]3)=[N:1][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 58548457Tert-butyl 3-(2-amino-4-methylphenylcarbamoyl)azetidine-1-carboxylateHCID 58548488Tert-butyl 3-(2-amino-5-methylphenylcarbamoyl)azetidine-1-carboxylate

Product 1

HCID 178423469HCID 178423469, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of tert-butyl 3-(2-amino-4-methylphenylcarbamoyl)azetidine-1-carboxylate and tert-butyl 3-(2-amino-5-methylphenylcarbamoyl)azetidine-1-carboxylate (prepared in the previous step) in AcOH (40 mL) was heated to 100° C. for 1.5 h and concentrated. The product tert-butyl 3-(5-methyl-1H-benzo[d]imidazol-2-yl)azetidine-1-carboxylate was used in the next step without further purification.

Workup

  1. concentrationconcentrated
  2. customThe product tert-butyl 3-(5-methyl-1H-benzo[d]imidazol-2-yl)azetidine-1-carboxylate was used in the next step without further purification

Sources & evidence

ORD record
ord-642238df95114d4fa20e813eb6d9de42
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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