Methyl iodide → HCID 131734404, compound

HRID 1509237Notes

Reaction equation

HRID 1509237 reaction equation
[CH3:1][C@H:2]1[O:7][C:6]2[N:8]=[C:9]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:27][CH2:26][CH2:25]4)=[CH:20][CH:19]=3)[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:11][C:5]=2[NH:4][C:3]1=[O:36].[C:37](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.C(OCC)(=O)C>[C:31]([O:30][C:29](=[O:35])[NH:28][C:24]1([C:21]2[CH:22]=[CH:23][C:18]([C:9]3[C:10]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)=[CH:11][C:5]4[N:4]([CH3:37])[C:3](=[O:36])[C@@H:2]([CH3:1])[O:7][C:6]=4[N:8]=3)=[CH:19][CH:20]=2)[CH2:25][CH2:26][CH2:27]1)([CH3:32])([CH3:34])[CH3:33]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67256413HCID 67256413, compound

Product 1

HCID 131734404HCID 131734404, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-tert-butyl 1-(4-(3-methyl-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutylcarbamate (100 mg, 0.206 mmol) in DMF (2 ml) was added potassium carbonate (85 mg) and iodomethane (15p1, 0.247 mmol). The reaction mixture was stirred at room temperature for 16 h then was diluted with ethyl acetate (20 ml). Washed with water, brine, and dried with Na2SO4, filtered and concentrated to give crude product which was purified by column (Biotage, size: 25 g) eluted with ethyl acetate/cyclohexane (0-50%) to afford product (33 mg). 1H NMR (500 MHz, CDCl3): 7.19-7.32 (m, 10H), 4.96 (q, 1H), 3.39 (s, 3H), 2.43-2.48 (m, 4H), 2.04 (m, 1H), 1.80 (m, 1H), 1.70 (d, 3H), 1.24-1.36 (m, 9H).

Workup

  1. washWashed with water, brine
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product which
  6. customwas purified by column (Biotage, size: 25 g)
  7. washeluted with ethyl acetate/cyclohexane (0-50%)

Sources & evidence

ORD record
ord-2f005e879eef46549929bf8cdc8701dd
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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