Sodium Carbonate → N-(cyanomethyl)-2-[(4-{[4-(2-fluoroethyl)piperazin-1-yl]carbonyl}phenyl)(phenyl)methoxy]-4-methylpentanamide

HRID 1180382Notes

Reaction equation

[C:1]([CH2:3][NH:4][C:5](=[O:33])[CH:6]([O:11][CH:12]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:13]1[CH:18]=[CH:17][C:16]([C:19]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[O:20])=[CH:15][CH:14]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2].C([O-])([O-])=O.[Na+].[Na+].Br[CH2:41][CH2:42][F:43]>C(#N)C>[C:1]([CH2:3][NH:4][C:5](=[O:33])[CH:6]([O:11][CH:12]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([N:21]2[CH2:22][CH2:23][N:24]([CH2:41][CH2:42][F:43])[CH2:25][CH2:26]2)=[O:20])=[CH:15][CH:14]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of N-(cyanomethyl)-4-methyl-2-{phenyl[4-(piperazin-1-ylcarbonyl)phenyl]methoxy}pentanamide from example 17, step 7 (79 mg, 0.18 mmol) in acetonitrile (1 mL), was added Na2CO3 (37 mg, 0.36 mmol) and 2-bromofluoroethane (39 μL, 0.525 mmol). The reaction was heated in a sealed tube at 85° C. for 16 hours and was then cooled down to room temperature. The mixture was then concentrated and the crude residue chromatographed on silica gel using 1% NH4OH and 9% methanol in dichloromethane to afford the title compound.

Workup

temperaturewas then cooled down to room temperature
concentrationThe mixture was then concentrated
customthe crude residue chromatographed on silica gel using 1% NH4OH and 9% methanol in dichloromethane

Sources & evidence

ORD record: ord-60f7ad280323434bbbb4e2210698a60b
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279478B2

Reaction notes

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