2,4-Dimethoxybenzaldehyde → HCID 18320739, compound

HRID 1699528Notes

Reaction equation

HRID 1699528 reaction equation
C(O[C:9](=O)[NH:10][CH:11]([C:23](=[O:25])[NH2:24])[C:12]([C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)=[O:13])C1C=CC=CC=1.[CH3:27][O:28][C:29]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:30]=1C=O>C(OCC)(=O)C.C(O)(=O)C.C(O)C.CN(C=O)C.CC(O)=O>[CH3:27][O:28][C:29]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:30]=1[CH2:9][NH:10][CH:11]([C:12]([C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)=[O:13])[C:23]([NH2:24])=[O:25]

Participants

5

Reactant 2

HCID 691752,4-DimethoxybenzaldehydeHCID 5086534HCID 5086534, compound

Product 1

HCID 18320739HCID 18320739, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 21925750HCID 21925750, compoundSolventHCID 21926011acetic acid N,N-dimethylformamideSolvent

Procedure

A solution of 2.0 g (5.69 mmol) of [1-carbamoyl-2-(3-indolyl)-2-oxoethyl]-carbamic acid benzyl ester in 160 ml ethyl acetate:acetic acid:ethanol (1:2:1) was hydrogenolyzed at atmospheric pressure over 0.45 g of 10% Pd(C) for 3 h. The mixture was filtered and concentrated. 2.41 g (11.4 mmol) of NaBH(OAc)4 was added in portions to a solution of the residue and 0.95 g (5.69 mmol) of 2,4-dimethoxybenzaldehyde in 30 ml of DMF:HOAc (1:1). After 18 h at room temperature the reaction mixture was concentrated and purified by chromatography on SiO2 (PhMe—CH2Cl2—MeOH—NEt3, 30:60:20:2). The solid product was washed with ether to give the title compound (1.78 g, 85%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. concentrationAfter 18 h at room temperature the reaction mixture was concentrated
  4. custompurified by chromatography on SiO2 (PhMe—CH2Cl2—MeOH—NEt3, 30:60:20:2)
  5. washThe solid product was washed with ether

Sources & evidence

ORD record
ord-aecab067ea24435ba67de24c85c12e61
Source dataset
uspto-grants-2002_02
Patent number
US06346625B1

Reaction notes

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