Sodium hydride → N-(1-Cyclopropanesulfonylaminocarbonyl-2-vinyl-cyclopropyl)-2-(hex-5-enyl-methyl-amino-carbonyl)-4-(2-chloropyrimidin-4-yloxy)-cyclopentane-carboxamide

HRID 1429156Notes

Reaction equation

HRID 1429156 reaction equation
[CH:1]1([S:4]([NH:7][C:8]([C:10]2([NH:15][C:16]([CH:18]3[CH2:22][CH:21]([OH:23])[CH2:20][CH:19]3[C:24]([N:26]([CH2:28][CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33])[CH3:27])=[O:25])=[O:17])[CH2:12][CH:11]2[CH:13]=[CH2:14])=[O:9])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[H-].[Na+].[Cl:36][C:37]1[N:42]=[C:41](Cl)[CH:40]=[CH:39][N:38]=1>CN(C=O)C>[CH:1]1([S:4]([NH:7][C:8]([C:10]2([NH:15][C:16]([CH:18]3[CH2:22][CH:21]([O:23][C:39]4[CH:40]=[CH:41][N:42]=[C:37]([Cl:36])[N:38]=4)[CH2:20][CH:19]3[C:24]([N:26]([CH2:28][CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33])[CH3:27])=[O:25])=[O:17])[CH2:12][CH:11]2[CH:13]=[CH2:14])=[O:9])(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 775312,4-DichloropyrimidineHCID 68589808N-(1-Cyclopropanesulfonylaminocarbonyl-2-vinyl-cyclopropyl)-2-(hex-5-enyl-methyl-amino-carbonyl)-4-hydroxy-cyclopentane-carboxamide

Product 1

HCID 72253694N-(1-Cyclopropanesulfonylaminocarbonyl-2-vinyl-cyclopropyl)-2-(hex-5-enyl-methyl-amino-carbonyl)-4-(2-chloropyrimidin-4-yloxy)-cyclopentane-carboxamideYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Compound 10e (43 mg, 89.3 mmol) was dissolved in DMF (2 ml) and the solution was cooled to 0° C. and NaH (11 mg, 0.27 mmol) was added. After 0.5 h 2,4-dichloro-pyrimidine was added. The reaction was stirred at 0° C. for 2 h and then quenched by addition of citric acid. The reaction mixture was extracted with DCM (3×10 ml) and the combined organic phases were washed with citric acid, water and brine. The organic phase was dried over MgSO4 and filtered. The solvent was removed in vacuo to yield the crude target compound (43 mg, 81%); LC/MS m/z (ESI+)=595 (MH+).

Workup

  1. customquenched by addition of citric acid
  2. extractionThe reaction mixture was extracted with DCM (3×10 ml)
  3. washthe combined organic phases were washed with citric acid, water and brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5145844a747c47c88d289c92704d2f7d
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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