Acetonitrile → HCID 66661304, compound

HRID 408874Notes

Reaction equation

HRID 408874 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:4]=1.[CH:16]1([CH2:20][NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([N:33]3[CH2:38][CH2:37]NCC3)=[O:32])=[CH:27][C:26]=2[F:39])=[O:23])[CH2:19][CH2:18]C1.C(=O)([O-])[O-].[K+].[K+].[C:46](#[N:48])[CH3:47]>>[C:12]([NH:11][C:9](=[O:10])[C:5]1[CH:4]=[C:3]([CH2:2][N:48]2[CH2:37][CH2:38][N:33]([C:31](=[O:32])[C:28]3[CH:29]=[CH:30][C:25]([NH:24][C:22]([NH:21][CH:20]4[CH2:18][CH2:19][CH2:16]4)=[O:23])=[C:26]([F:39])[CH:27]=3)[CH2:47][CH2:46]2)[CH:8]=[CH:7][N:6]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 66661338HCID 66661338, compoundHCID 66661596HCID 66661596, compound

Product 1

HCID 66661304HCID 66661304, compound

Procedure

4-(Bromomethyl)-N-tert-butylpicolinamide (70 mg, 0258 mmol), 1-(cyclobutyl-methyl)-3-(2-fluoro-4-(piperazine-1-carbonyl)phenyl)urea (83 mg, 0.258 mmol) and potassium carbonate (106 mg, 0.744 mmol) were combined and heated to reflux in acetonitrile for 1 hour. The reaction mixture was concentrated at reduced pressure and the resulting residue purified by reverse phase acidic preparative HPLC to afford the title compound (41 mg). MS (ESI) m/z 511.6 [M+H]+

Workup

  1. temperatureheated
  2. concentrationThe reaction mixture was concentrated at reduced pressure
  3. customthe resulting residue purified by reverse phase acidic preparative HPLC

Sources & evidence

ORD record
ord-ecaeceb982014d19895932ecdd41ac67
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

Loading…