Methyl iodide → HCID 131734403, compound

HRID 1509141Notes

Reaction equation

HRID 1509141 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:20][C:21]4[NH:26][CH2:25][CH2:24][O:23][C:22]=4[N:27]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:37]I.[NH4+].[Cl-]>CN(C=O)C>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:19]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[CH:20][C:21]4[N:26]([CH3:37])[CH2:25][CH2:24][O:23][C:22]=4[N:27]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 123843496HCID 123843496, compound

Product 1

HCID 131734403HCID 131734403, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl(1-(4-(7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (20 mg, 0.04 mmol) in dry DMF (1 ml) at 0° C. was added sodium hydride (2 mg, 0.05 mmol) and methyl iodide (5 μl, 0.05 mmol) under nitrogen. The resulting mixture was stirred for 30 minutes at 0° C. A saturated solution of NH4Cl was added and the mixture was extracted with DCM (3×10 ml). The combined organic phases were dried over Na2SO4 and concentrated to dryness under reduced pressure. The resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 20% EtOAc in cyclohexane) to give the title compound (8 mg, 44%). 1H NMR (500 MHz, CDCl3): 7.39-7.19 (9H, m), 6.85 (1H, s), 4.51-4.50 (2H, d), 3.45-3.43 (2H, d), 2.80-2.70 (2H, m), 2.61-2.51 (4H, m), 2.01-1.88 (1H, m), 2.00 (3H, s), 1.40-1.10 (9H, br).

Workup

  1. extractionthe mixture was extracted with DCM (3×10 ml)
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 20% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-8451986587d840118ebac20df4535362
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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