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Water → N-[6-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-1-(1-methylethyl)-1H-pyrazole-5-carboxamide

HRID 244679
Notes
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Reaction equation

HRID 244679 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:17])[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH:6]=2.CCN(C(C)C)C(C)C.[CH3:27][CH:28]([N:30]1[C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=[N:31]1)[CH3:29].O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:17][C:35]([C:34]2[N:30]([CH:28]([CH3:29])[CH3:27])[N:31]=[CH:32][CH:33]=2)=[O:36])[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH:6]=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 582557836-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine2×HCID 583564221-Isopropyl-1H-pyrazole-5-carbonyl chloride

Product 1

HCID 58255796N-[6-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-1-(1-methylethyl)-1H-pyrazole-5-carboxamideYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

6-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (2.25 g, 7.59 mmol) was dissolved in DCM (40 ml) and DIPEA (2.85 ml, 16.34 mmol) was added. 1-(1-methylethyl)-1H-pyrazole-5-carbonyl chloride (1.41 g, 8.17 mmol) in DCM (10 ml) was added and the mixture left to stir at room temperature overnight. Water (50 ml) was added and the mixture vigorously stirred. The DCM layer was passed through a hydrophobic frit and evaporated to dryness. The material was combined with that obtained from a previous smaller scale reaction carried out in an identical manner but starting with 6-bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (0.2 g, 0.675 mmol). The combined crude materials were purified by chromatography on silica using a 50 g cartridge and eluting progressively with DCM, then 1-4% methanol in DCM. Product containing fractions were combined and evaporated to dryness to afford the title compound (2.8 g).

Workup

  1. waitthe mixture left
  2. stirringthe mixture vigorously stirred
  3. customevaporated to dryness
  4. customthat obtained from a previous smaller scale reaction
  5. customwere purified by chromatography on silica using a 50 g cartridge
  6. washeluting progressively with DCM
  7. additionProduct containing fractions
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-751bf8f8f1034e5097eb172ab85f098c
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658635B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes