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1,4-Dioxane → N-1H,1'H-4,6'-Biindazol-4'-yl-2-methyl-1,3-thiazole-4-carboxamide

HRID 244748
Notes
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Reaction equation

HRID 244748 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:17][C:18]([C:20]2[N:21]=[C:22]([CH3:25])[S:23][CH:24]=2)=[O:19])[C:5]2[C:9]([CH:10]=1)=[N:8][N:7](C1CCCCO1)[CH:6]=2.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC1(C)C(C)(C)OB([C:42]2[CH:50]=[CH:49][CH:48]=[C:47]3[C:43]=2[CH:44]=[N:45][NH:46]3)O1.O1CCOCC1>CO.O>[NH:46]1[C:47]2[CH:48]=[CH:49][CH:50]=[C:42]([C:2]3[CH:10]=[C:9]4[C:5]([CH:6]=[N:7][NH:8]4)=[C:4]([NH:17][C:18]([C:20]4[N:21]=[C:22]([CH3:25])[S:23][CH:24]=4)=[O:19])[CH:3]=3)[C:43]=2[CH:44]=[N:45]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 58255778N-[6-bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

Product 1

HCID 58356442N-1H,1'H-4,6'-Biindazol-4'-yl-2-methyl-1,3-thiazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A microwave vial was charged with N-[6-bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide (50 mg), Solvias catalyst (7 mg), tripotassium phosphate (101 mg), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (available from J&W Pharmlab, 29 mg), 1,4-dioxane (0.5 ml) and water (0.1 ml). The reaction was heated under microwave irradiation for a total of 60 min at 80° C., then 30 min at 120° C. The reaction was passed through a silica cartridge preconditioned with methanol, washing with methanol, then dried in vacuo. The residue was subjected to a DCM/water wash, dried through a hydrophobic frit and dried in vacuo. The residue was dissolved in DMSO:methanol (1 ml, 1:1, v/v) and purified by MDAP (Method D). Appropriate fractions were evaporated under a stream of nitrogen. The residue was dissolved in methanol and a few drops of 2M HCl (aq) were added and the reaction was stirred for 30 min. The reaction was diluted with methanol and passed through an aminopropyl cartridge, pre-conditioned with methanol, washing with methanol, then dried to give title compound, 11 mg.

Workup

  1. custom30 min
  2. customat 120° C
  3. washwashing with methanol
  4. customdried in vacuo
  5. washwash
  6. customdried through a hydrophobic frit
  7. customdried in vacuo
  8. dissolutionThe residue was dissolved in DMSO
  9. custommethanol (1 ml, 1:1, v/v) and purified by MDAP (Method D)
  10. customAppropriate fractions were evaporated under a stream of nitrogen
  11. dissolutionThe residue was dissolved in methanol
  12. additiona few drops of 2M HCl (aq) were added
  13. additionThe reaction was diluted with methanol
  14. washwashing with methanol
  15. customdried

Sources & evidence

ORD record
ord-96281302ccac434bab065987fb0fbcd4
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658635B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes