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Cesium carbonate → N-[6-Amino-5-(2,3-dichloro-5-methoxyphenyl)pyrazin-2-yl]-1-methyl-1H-pyrazole-5-carboxamide

HRID 2100344
Notes
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Reaction equation

HRID 2100344 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=2)=[O:10])[CH:5]=[N:4][C:3]=1Cl.[Cl:18][C:19]1[C:24]([Cl:25])=[CH:23][C:22]([O:26][CH3:27])=[CH:21][C:20]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=2)=[O:10])[CH:5]=[N:4][C:3]=1[C:20]1[CH:21]=[C:22]([O:26][CH3:27])[CH:23]=[C:24]([Cl:25])[C:19]=1[Cl:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 577991422-(2,3-Dichloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 57799151N-(6-Amino-5-chloropyrazin-2-yl)-1-methyl-1H-pyrazole-5-carboxamide

Product 1

HCID 16661733N-[6-Amino-5-(2,3-dichloro-5-methoxyphenyl)pyrazin-2-yl]-1-methyl-1H-pyrazole-5-carboxamideYield 46.2%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

N-(6-Amino-5-chloropyrazin-2-yl)-1-methyl-1H-pyrazole-5-carboxamide (Preparation 2, 0.1 g, 0.396 mmol) was combined with 2,(2,3-dichloro-5-methoxy-phenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Preparation 18), (0.156 g, 0.515 mmol), cesium carbonate (0.129 g, 0.396 mmol) and palladium tetrakistriphenylphosphine (0.046 g, 0.04 mmol) and suspended in a mixture of 1,4-dioxane (1 ml) and water (0.5 ml). The reaction was heated at 80° C. for 5 hours. The reaction was allowed to cool to room temperature and then concentrated in vacuo. The residue was partitioned between aqueous sodium carbonate solution (20 ml) and ethyl acetate (20 ml) and the organic layer dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography, eluting with ethyl acetate:heptane 2:3 to 1:1, to afford the product as an off-white solid (72 mg).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between aqueous sodium carbonate solution (20 ml) and ethyl acetate (20 ml)
  4. dry with materialthe organic layer dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with ethyl acetate:heptane 2:3 to 1:1

Sources & evidence

ORD record
ord-77967d77034746c58e84c6a0fdda7bf8
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07572797B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes