1-Hydroxybenzotriazole → HCID 86678164, compound

HRID 82028Notes

Reaction equation

HRID 82028 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:18]([OH:20])=O)[C:5]2[C:10]([I:11])=[N:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:6]=2[N:7]=1.[C:21]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>O1CCCC1.CN(C)C(=O)C>[C:24]([O:23][C:21]([N:28]1[CH2:33][CH2:32][N:31]([C:18]([C:4]2[C:5]3[C:10]([I:11])=[N:9][N:8]([CH:12]4[CH2:17][CH2:16][CH2:15][CH2:14][O:13]4)[C:6]=3[N:7]=[C:2]([Cl:1])[CH:3]=2)=[O:20])[CH2:30][CH2:29]1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86678163HCID 86678163, compound

Product 1

HCID 86678164HCID 86678164, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 6-chloro-3-iodo-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (17 g, 42 mmol) in a mixture of tetrahydrofuran (250 mL) and N,N-dimethylacetamide (40 mL) were added 1-boc-piperazine (8.6 g, 46 mmol), 1-hydroxybenzotriazole (0.56 g, 4.2 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (8.03 g, 42 mmol). The reaction mixture was stirred at room temperature for 20 hours and then the THF was evaporated under vacuum. An aqueous solution of bicarbonate (200 mL) was then added and the mixture stirred for 1 hour. The precipitate was filtered, washed with water, and then dried to afford the title compound as a yellow solid (24 g, 100%).

Workup

  1. customthe THF was evaporated under vacuum
  2. additionAn aqueous solution of bicarbonate (200 mL) was then added
  3. stirringthe mixture stirred for 1 hour
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-04474d57a43e4328b9bac7bcd910cb3a
Source dataset
uspto-grants-2014_09
Patent number
US08846712B2

Reaction notes

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