Water → HCID 68595849, compound

HRID 220591Notes

Reaction equation

HRID 220591 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:16]=[N:17][N:18]([CH3:21])[C:19]=3[CH3:20])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[CH3:22][O:23][C:24]([NH:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)=[O:25].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[ClH:1].[CH3:22][O:23][C:24](=[O:25])[NH:26][C:27]1[CH:28]=[CH:29][C:30]([C:2]2[C:3]([N:8]3[CH2:13][CH2:12][N:11]([CH2:14][C:15]4[CH:16]=[N:17][N:18]([CH3:21])[C:19]=4[CH3:20])[CH2:10][CH2:9]3)=[N:4][CH:5]=[CH:6][N:7]=2)=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27734944-(Methoxycarbonylamino)phenylboronic acidHCID 594382163'-chloro-4-(1,5-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

Product 1

HCID 68595849HCID 68595849, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31374DimethylacetamideSolvent

Procedure

Stir together 3′-chloro-4-(1,5-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (307 mg, 1.00 mmol), 4-(methoxycarbonylamino)benzene boronic acid (234 mg, 1.2 mmol), potassium carbonate (332 mg, 2.4 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.006 g, 0.005 mmol) and water (2 mL), in N,N-dimethylacetamide (4 mL) at room temperature under nitrogen, then heat at 120° C. for 5 hr. Cool to room temperature, purify using SCX chromatography and further purify using silica gel chromatography eluting with (5:95 to 15:85 methanol:DCM). Dissolve in acetonitrile, and add 2 M aq. HCl and water then lyophilize to give the title compound as light yellow powder (253 mg, 55%). MS (ES): m/z=422 [M+H].

Workup

  1. custompurify
  2. customfurther purify
  3. washeluting with (5:95 to 15:85 methanol:DCM)
  4. dissolutionDissolve in acetonitrile
  5. additionadd 2 M aq. HCl and water

Sources & evidence

ORD record
ord-df23b27fbb2e4f5bb9bd8d6f75a1bd27
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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