Triethylamine → HCID 66680993, compound

HRID 239877Notes

Reaction equation

HRID 239877 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[C:6]2[C:10]=1[NH:9][N:8]=[C:7]2[NH2:11].[CH3:21][N:22]([CH3:27])[C:23](=[O:26])[CH:24]=[CH2:25].C(N(CC)CC)C>C1COCC1>[NH2:11][C:7]1[C:6]2[C:10](=[C:2](/[CH:25]=[CH:24]/[C:23]([N:22]([CH3:27])[CH3:21])=[O:26])[CH:3]=[CH:4][C:5]=2[C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[NH:9][N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 17587N,N-DimethylacrylamideHCID 66680566HCID 66680566, compound

Product 1

HCID 66680993HCID 66680993, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 84B (165 mg), N,N-dimethylacrylamide (0.102 mL), triethylamine (0.207 mL), and Pd(o-tol3P)2Cl2 (30 mg) in THF (2 mL) in a sealed tube was heated in a Smith Synthesizer microwave oven (at 300 W) to 150° C. and concentrated. The residue was purified by flash column chromatography on silica gel with 3% methanol/dichloromethane to provide 163 mg of the desired product. MS (ESI(+)) m/e 352 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash column chromatography on silica gel with 3% methanol/dichloromethane

Sources & evidence

ORD record
ord-cbf2be0446cf45fcaf7f60559010f89a
Source dataset
uspto-grants-2014_02
Patent number
US08642776B2

Reaction notes

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