2,4-Dimethoxybenzylamine → 4-{4-[4-(2,4-Dimethoxy-benzylcarbamoyl)-oxazol-5-yl]-phenyl}-2,2-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 2278384Notes

Reaction equation

HRID 2278384 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[O:24][CH:23]=[N:22][C:21]=3[C:25]([OH:27])=O)=[CH:16][CH:15]=2)[CH2:10][C:9]1([CH3:29])[CH3:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:30][O:31][C:32]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:33]=1[CH2:34][NH2:35].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[O:24][CH:23]=[N:22][C:21]=3[C:25](=[O:27])[NH:35][CH2:34][C:33]3[CH:36]=[CH:37][C:38]([O:40][CH3:41])=[CH:39][C:32]=3[O:31][CH3:30])=[CH:18][CH:19]=2)[CH2:10][C:9]1([CH3:29])[CH3:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 5972502,4-DimethoxybenzylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 897392914-[4-(4-Carboxy-oxazol-5-yl)-phenyl]-2,2-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 897392824-{4-[4-(2,4-Dimethoxy-benzylcarbamoyl)-oxazol-5-yl]-phenyl}-2,2-dimethyl-piperazine-1-carboxylic acid tert-butyl esterYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[4-(4-Carboxy-oxazol-5-yl)-phenyl]-2,2-dimethyl-piperazine-1-carboxylic acid tert-butyl ester was dissolved in 30 mL DMF. To the solution was added 2,4-dimethoxybenzylamine (1.26 g, 7.6 mmol), HATU (2.8 g, 7.4 mmol) and TEA (1 g, 10 mmol). The mixture was stirred at room temperature overnight and the solvent was removed in vacuo. The residue was purified by silica gel column chromatography (PE:EtOAc=5:1 to DCM:MeOH=200:1) to afford the title compound (1.6 g, 3 mmol, yield: 54% over two steps).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by silica gel column chromatography (PE:EtOAc=5:1 to DCM:MeOH=200:1)

Sources & evidence

ORD record
ord-a868429ce6934e23bfbe02dccb5b8c1f
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

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