Sodium hydride → HCID 123922698, compound

HRID 1509164Notes

Reaction equation

HRID 1509164 reaction equation
[O:1]=[C:2]1[CH2:7][O:6][C:5]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:4]=2[NH:3]1.[H-].[Na+].Br[CH:39]([CH3:42])[C:40]#[N:41]>CN(C=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:4]4[N:3]([CH:39]([C:40]#[N:41])[CH3:42])[C:2](=[O:1])[CH2:7][O:6][C:5]=4[N:8]=3)=[CH:19][CH:20]=2)[CH2:25][CH2:26][CH2:27]1)([CH3:32])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1405382-BromopropionitrileHCID 67256382HCID 67256382, compound

Product 1

HCID 123922698HCID 123922698, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 50 ml round bottom flask was added tert-butyl 1-(4-(2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutylcarbamate (50 mg, 0.106 mmol) in DMF (Volume: 4 ml) to give a brown solution. sodium hydride (10.18 mg, 0.254 mmol) and 2-bromopropanenitrile (17.05 mg, 0.127 mmol) were added. The reaction mixture was stirred at 50 degree for 1 h then room temperature overnight. The reaction mixture was partitioned between DCM (20 ml) and water (20 ml). The organic phase was separated and concentrated. The residue was purified by column (biotage, 25 g) eluted with ethyl acetate/cyclohexane (0-50%) to give product (19 mg). LCMS (Method A): RT=7.14 min, M+H+=525.0.

Workup

  1. customto give a brown solution
  2. customroom temperature overnight
  3. customThe reaction mixture was partitioned between DCM (20 ml) and water (20 ml)
  4. customThe organic phase was separated
  5. concentrationconcentrated
  6. customThe residue was purified by column (biotage, 25 g)
  7. washeluted with ethyl acetate/cyclohexane (0-50%)

Sources & evidence

ORD record
ord-93343ba399a94551a1faf497acc98b7f
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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