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N-bromobutanimide → 2-(4-(1-(Pyrazolo[1,5-a]pyridin-5-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)-1H-pyrazol-1-yl)ethanol

HRID 1890613
Notes
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Reaction equation

HRID 1890613 reaction equation
[N:1]1[N:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]3[C:15]4=[N:16][C:17]([C:20]5[CH:21]=[N:22][N:23]([CH2:25][CH2:26][O:27]C6CCCCO6)[CH:24]=5)=[CH:18][N:19]=[C:14]4[N:13]=[N:12]3)=[CH:9][C:4]2=[CH:3][CH:2]=1.C1C(=O)N(Br)C(=O)C1>C(Cl)(Cl)Cl>[N:1]1[N:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]3[C:15]4=[N:16][C:17]([C:20]5[CH:21]=[N:22][N:23]([CH2:25][CH2:26][OH:27])[CH:24]=5)=[CH:18][N:19]=[C:14]4[N:13]=[N:12]3)=[CH:9][C:4]2=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 682894141-(pyrazolo[1,5-a]pyridin-5-ylmethyl)-6-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine

Product 1

HCID 532625182-(4-(1-(Pyrazolo[1,5-a]pyridin-5-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)-1H-pyrazol-1-yl)ethanol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-(pyrazolo[1,5-a]pyridin-5-ylmethyl)-6-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine 311-a (10 mg, 0.022 mmol) (prepared according to the procedure of Compound 1) in CHCl3 was added NBS (4.4 mg, 0.025 mmol). The reaction mixture was stirred at rt for 1 h, then concentrated. The resulting residue was dissolved in CHCl3 (2 mL) and MeOH (2 mL), followed by the addition of 6N HCl in MeOH. The resulting mixture was stirred for 30 min, then treated with NH3.H2O to bring pH to 8. The mixture was concentrated and purified by prep-TLC to afford the title compound. MS (m/z): 439.9 (M+1)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe resulting residue was dissolved in CHCl3 (2 mL)
  3. additionMeOH (2 mL), followed by the addition of 6N HCl in MeOH
  4. stirringThe resulting mixture was stirred for 30 min
  5. additiontreated with NH3.H2O
  6. concentrationThe mixture was concentrated
  7. custompurified by prep-TLC

Sources & evidence

ORD record
ord-2897bbc941f84bbd86631e0d4f4c5b9a
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08507487B2

Reaction notes

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