HCID 18506862, compound → HCID 18506796, compound

HRID 1355477Notes

Reaction equation

HRID 1355477 reaction equation
CON(C)[C:4]([C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:7]=1)=[O:5].[CH3:21][Mg+].[Br-]>C1COCC1>[C:4]([C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH:7]=1)(=[O:5])[CH3:21]

Participants

4

Reactant 2

HCID 18506862HCID 18506862, compoundHCID 178418689HCID 178418689, compound2×

Product 1

HCID 18506796HCID 18506796, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4{[methoxy(methyl)amino]carbonyl}pyridin-2-ylcarbamate (16-2, 224 mg, 0.8 mmole) in dry THF (5 mL) was added MeMgBr (0.6 mL, 3 M in Et2O, 1.75 mmole) at −20° C. After 30 minutes the mixture was warmed to RT. After 30 minutes additional MeMgBr (0.3 mL) was added. After 1 hr the mixture was quenched with saturated NH4Cl and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated to give the titled compound as an off-white solid which was sufficiently pure for use in the next step. 1H-NMR (500 MHz, (CDCl3) δ8.44 (s, 1H), 8.40 (d, 1H, J=5.13 Hz), 8.02 (bs, 1H), 7.41 (d, 1H, J=5.13 Hz), 2.64 (s, 3H), 1.56 (s, 9H).

Workup

  1. customAfter 1 hr the mixture was quenched with saturated NH4Cl
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-02f93bb00d4e4909ae297f3eb5942f95
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

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