Ammonium Chloride → HCID 178424501, compound

HRID 1711258Notes

Reaction equation

HRID 1711258 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:20]2[CH2:25][CH2:24][C:23]([CH3:27])([CH3:26])[CH2:22][CH:21]=2)=[C:8]([NH:10][C:11]([C:13]2[NH:14][CH:15]=[C:16]([C:18]#[N:19])[N:17]=2)=[O:12])[CH:9]=1)(=[O:3])[CH3:2].[CH3:28][Mg]Cl.[NH4+].[Cl-]>C1COCC1.[Cl-].[Na+].O>[CH3:26][C:23]1([CH3:27])[CH2:24][CH2:25][C:20]([C:7]2[CH:6]=[CH:5][C:4]([C:1]([OH:3])([CH3:28])[CH3:2])=[CH:9][C:8]=2[NH:10][C:11]([C:13]2[NH:14][CH:15]=[C:16]([C:18]#[N:19])[N:17]=2)=[O:12])=[CH:21][CH2:22]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 178418332HCID 178418332, compoundHCID 178466077HCID 178466077, compound

Product 1

HCID 178424501HCID 178424501, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4-cyano-1H-imidazole-2-carboxylic acid [5-acetyl-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in Example 31, step (d), 30.0 mg, 0.0828 mmol) in 2 mL of THF at −78° C. under Ar was added methyl magnesium chloride (58 μL, 0.17 mmol, 3.0 M in THF). The resulting mixture was warmed to RT and stirred for 0.5 h. Treated with 10 mL of saturated NH4Cl aqueous solution followed by 10 mL of brine, the mixture was extracted with EtOAc (2×20 mL). The combined organic layers were dried with Na2SO4. The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (2-3% MeOH/DCM) to give 29.0 mg (93%) of the title compound as a white solid. 1H-NMR (DMSO-d6; 400 MHz): δ 14.22 (s, 1H), 9.76 (s, 1H), 8.32 (s, 1H), 8.12 (d, 1H, J=1.8 Hz), 7.25 (dd, 1H, J=8.1, 1.8 Hz), 7.14 (d, 1H, J=8.1 Hz), 5.65 (m, 1H), 2.16-2.29 (m, 2H), 1.87-1.98 (m, 2H), 1.47 (t, 2H, J=6.2 Hz), 1.43 (s, 6H), 0.99 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C22H26N4O2, 379.2 (M+H), found 379.0.

Workup

  1. extractionthe mixture was extracted with EtOAc (2×20 mL)
  2. dry with materialThe combined organic layers were dried with Na2SO4
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel (2-3% MeOH/DCM)

Sources & evidence

ORD record
ord-76537de61e1e45448735fba36349aed3
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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