4-Methyloxazole → [2-Amino-6-(4-methyl-oxazol-2-yl)-3-nitro-pyridin-4-yl]-(3-cyano-benzyl)-carbamic acid ethyl ester

HRID 639676Notes

Reaction equation

HRID 639676 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][O:5][CH:6]=1.[CH2:7]([O:9][C:10](=[O:32])[N:11]([C:21]1[CH:26]=[C:25](Br)[N:24]=[C:23]([NH2:28])[C:22]=1[N+:29]([O-:31])=[O:30])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[N:20])[CH:14]=1)[CH3:8]>[Cl-].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd+2]>[CH2:7]([O:9][C:10](=[O:32])[N:11]([C:21]1[CH:26]=[C:25]([C:4]2[O:5][CH:6]=[C:2]([CH3:1])[N:3]=2)[N:24]=[C:23]([NH2:28])[C:22]=1[N+:29]([O-:31])=[O:30])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[N:20])[CH:14]=1)[CH3:8]

Participants

4

Reactant 2

HCID 696634-MethyloxazoleHCID 86614489(2-Amino-6-bromo-3-nitro-pyridin-4-yl)-(3-cyano-benzyl)-carbamic acid ethyl ester

Product 1

HCID 67457807[2-Amino-6-(4-methyl-oxazol-2-yl)-3-nitro-pyridin-4-yl]-(3-cyano-benzyl)-carbamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 84124Bis(triphenylphosphine)palladium chlorideCatalyst

Procedure

The title compound was prepared following the example in preparation 70, using 4-methyl-oxazole (40 mg), (2-amino-6-bromo-3-nitro-pyridin-4-yl)-(3-cyano-benzyl)-carbamic acid ethyl ester (100 mg) and palladium bis(triphenylphosphine)dichloride (30 mg), giving the product (65 mg) as a yellow solid.

Workup

  1. customin preparation 70

Sources & evidence

ORD record
ord-3ffaee8913224cc381b198441741336f
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

Loading…