Ethyl Bromide → HCID 60151777, compound

HRID 1406013Notes

Reaction equation

HRID 1406013 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([C:14]1[C:18]2[CH2:19][CH2:20][CH2:21][C:22]3[C:23](=[N:24][C:25]([NH:28][C:29]4[CH:34]=[CH:33][C:32]([N:35]5[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]5)=[CH:31][C:30]=4[O:42][CH3:43])=[N:26][CH:27]=3)[C:17]=2[NH:16][N:15]=1)=[O:13])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:51][CH3:52]>CN(C=O)C>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([C:14]1[C:18]2[CH2:19][CH2:20][CH2:21][C:22]3[C:23](=[N:24][C:25]([NH:28][C:29]4[CH:34]=[CH:33][C:32]([N:35]5[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]5)=[CH:31][C:30]=4[O:42][CH3:43])=[N:26][CH:27]=3)[C:17]=2[N:16]([CH2:51][CH3:52])[N:15]=1)=[O:13])[CH3:2]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 10796Cesium carbonateHCID 178436231HCID 178436231, compound

Product 1

HCID 60151777HCID 60151777, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(2,6-diethylphenyl)-9-{[2-methoxy-4-(4-methylpiperazin-1-yl)phenyl]amino}-1,4,5,6-tetrahydropyrazolo[4′,3′:6,7]cyclohepta[1,2-d]pyrimidine-3-carboxamide (0.065 g, 0.11 mmol) in DMF (1.1 mL), Cs2CO3 (0.073 g, 0.22 mmol) and bromoethane (0.008 mL, 0.11 mmol) were added. The mixture was stirred at room temperature for 12 h, solvent was removed under vacuo, then DCM (10 mL) was added and the organic phase washed with water (2×15 mL). The organic fraction was, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (eluant: DCM/MeOH95/5) provided 30 mg (30%) of the title compound as a pale yellow solid.

Workup

  1. customsolvent was removed under vacuo
  2. additionDCM (10 mL) was added
  3. washthe organic phase washed with water (2×15 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel (eluant: DCM/MeOH95/5)

Sources & evidence

ORD record
ord-e86b2c0293fb42e3beecca1f319d092a
Source dataset
uspto-grants-2014_12
Patent number
US08916577B2

Reaction notes

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