Acetonitrile → HCID 58055793, compound

HRID 408876Notes

Reaction equation

HRID 408876 reaction equation
CS(O[CH2:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=1)(=O)=O.C1([CH2:21][NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([N:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)=[O:33])=[CH:28][C:27]=2[F:40])=[O:24])CCC1.[C:41](=O)([O-])[O-].[K+].[K+].[C:47](#N)[CH3:48]>>[CH:21]1([NH:22][C:23](=[O:24])[NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([N:34]3[CH2:35][CH2:36][N:37]([CH2:6][C:7]4[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=4)[CH2:38][CH2:39]3)=[O:33])=[CH:28][C:27]=2[F:40])[CH2:48][CH2:47][CH2:41]1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 54451634Methyl 6-((methylsulfonyloxy)methyl)picolinateHCID 66661596HCID 66661596, compound

Product 1

HCID 58055793HCID 58055793, compound

Procedure

Methyl 6-((methylsulfonyloxy)methyl)picolinate (300 mg, 1.22 mmol), 1-(cyclo-butylmethyl)-3-(2-fluoro-4-(piperazine-1-carbonyl)phenyl)urea (391 mg, 1.22 mmol) and potassium carbonate (505 mg, 3.66 mmol) were combined and stirred in acetonitrile for 18 hours. The reaction mixture was concentrated at reduced pressure. The resulting residue was taken up in dichloromethane, washed with water, dried over sodium sulfate and concentrated under vacuum to afford the title compound (407 mg).

Workup

  1. concentrationThe reaction mixture was concentrated at reduced pressure
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-241998b514e9442493a198ec4a6ba01a
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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