HCID 86584332, compound → HCID 69900893, compound

HRID 2308010Notes

Reaction equation

HRID 2308010 reaction equation
[CH3:1][Mg+].[Br-].[Cl:4][C:5]1[CH:27]=[C:26]([CH3:28])[C:8]([O:9][C:10]2[N:18]=[C:17]([CH3:19])[CH:16]=[C:15]([NH:20][CH:21]([CH:24]=[O:25])[CH2:22][CH3:23])[C:11]=2[C:12]([NH2:14])=[O:13])=[C:7]([CH3:29])[CH:6]=1>C1COCC1>[Cl:4][C:5]1[CH:6]=[C:7]([CH3:29])[C:8]([O:9][C:10]2[N:18]=[C:17]([CH3:19])[CH:16]=[C:15]([NH:20][CH:21]([CH2:22][CH3:23])[CH:24]([OH:25])[CH3:1])[C:11]=2[C:12]([NH2:14])=[O:13])=[C:26]([CH3:28])[CH:27]=1

Participants

4

Reactant 2

HCID 86584332HCID 86584332, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 69900893HCID 69900893, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of MeMgBr in dry THF was added a solution of 2-(4-chloro-2,6-dimethyl-phenoxy)-4-(1-formyl-propylamino)-6-methyl-nicotinamide in dry THF at −78° C. The mixture was stirred at −78° C. for 2 hr, then quenched with dilute acid. After standard extraction and purification, the title compound was obtained. 1H NMR(CDCl3) d 9.8(d,1H), 7.9(nbrs,1H), 7.05(s,2H), 6.27(s,0.5H), 6.24(s,0.5H), 5.6(brs,1H), 3.91(m,0.5H), 3.89(m,0.5H), 3.51(m,0.5H), 3.3(m,0.5H), 2.09(s,9H), 1.5-1.8(m,2H), 1.26(d,3H), 0.98(t,3H) ppm.

Workup

  1. customquenched
  2. additionwith dilute acid
  3. extractionAfter standard extraction and purification

Sources & evidence

ORD record
ord-8d8c62aa90ec43ed8a1ef3673e475fd3
Source dataset
uspto-grants-2004_12
Patent number
US06833378B2

Reaction notes

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