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1,4-Dioxane → 1-(1-(3-chlorophenyl)-1H-pyrazol-4-yl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide

HRID 1473619
Notes
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Reaction equation

HRID 1473619 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([NH:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][N:17]=3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Cl:22][C:23]1[CH:24]=[C:25]([N:29]2[CH:33]=[C:32](B(O)O)[CH:31]=[N:30]2)[CH:26]=[CH:27][CH:28]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>O>[Cl:22][C:23]1[CH:24]=[C:25]([N:29]2[CH:33]=[C:32]([C:2]3[C:11]4[C:6](=[CH:7][C:8]([S:12]([NH:15][C:16]5[CH:21]=[CH:20][N:19]=[CH:18][N:17]=5)(=[O:14])=[O:13])=[CH:9][CH:10]=4)[CH:5]=[CH:4][N:3]=3)[CH:31]=[N:30]2)[CH:26]=[CH:27][CH:28]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 467386771-(3-Chlorophenyl)pyrazole-4-boronic acidHCID 866876591-chloro-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide

Product 1

HCID 866876871-(1-(3-chlorophenyl)-1H-pyrazol-4-yl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A vial was charged with 1-chloro-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (Intermediate GG) (53 mg, 0.17 mmol), (1-(3-chlorophenyl)-1H-pyrazol-4-yl)boronic acid (44 mg, 0.200 mmol), Pd(AmPhos)2Cl2 (12 mg, 0.017 mmol), potassium phosphate (106 mg, 0.500 mmol), dioxane (1.042 μl), and water (0.347 μl). The vial was sealed and heated in an oil bath overnight at 100° C. The crude reaction mixture was purified using reverse-phase HPLC with a Waters-Xbridge C18, 19×100 mm, 10 μm column with a gradient 5-95% acetonitrile and water with 0.1% ammonium hydroxide modifier to yield 1-(1-(3-chlorophenyl)-1H-pyrazol-4-yl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide. m/z (ESI) 463.0 (M+H)+.

Workup

  1. customThe vial was sealed
  2. customThe crude reaction mixture
  3. customwas purified

Sources & evidence

ORD record
ord-e167497645c245a49ce4be6dd57fc10a
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09012443B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes