Benzylamine → HCID 67426830, compound

HRID 2235449Notes

Reaction equation

HRID 2235449 reaction equation
[N+](C1C=CC([O:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([NH:25][C:26](=[O:35])[C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=3)[C:15]([CH3:37])([CH3:36])[C:14]2=[O:38])=O)=CC=1)([O-])=O.[CH2:39]([NH2:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[CH2:39]([NH:46][C:11]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([NH:25][C:26](=[O:35])[C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=2)[C:15]([CH3:36])([CH3:37])[C:14]1=[O:38])=[O:10])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 86601808HCID 86601808, compound

Product 1

HCID 67426830HCID 67426830, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(4-methoxy-benzoylamino)-3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-indole-1-carboxylic acid 4-nitro-phenyl ester (54 mg) in CH2Cl2 (10 ml) is added benzyl amine (44 μl) at RT. The reaction mixture is stirred at RT for 20 h. After an aqueous work-up and concentration in vacuo, the residue is dissolved in acetic acid (3 ml) and iron (60 mg; powder) is added. The mixture is stirred in a microwave apparatus at 150° C. for 900 s. After filtration and evaporation of the solvent the crude material is purified by preparative RP-HPLC.

Workup

  1. concentrationAfter an aqueous work-up and concentration in vacuo
  2. dissolutionthe residue is dissolved in acetic acid (3 ml)
  3. additioniron (60 mg; powder) is added
  4. stirringThe mixture is stirred in a microwave apparatus at 150° C. for 900 s
  5. filtrationAfter filtration and evaporation of the solvent the crude material
  6. customis purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-9076e5a5e7f140d38373f6dba46c90ff
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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