Triethylamine → 1-trityl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 44674Notes

Reaction equation

HRID 44674 reaction equation
[C:1]([N:20]1[C:24]2[N:25]=[CH:26][CH:27]=[C:28]([C:29](O)=[O:30])[C:23]=2[CH:22]=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:34](CC)CC)C.[Cl-].[NH4+].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.C(Cl)Cl>[C:1]([N:20]1[C:24]2[N:25]=[CH:26][CH:27]=[C:28]([C:29]([NH2:34])=[O:30])[C:23]=2[CH:22]=[N:21]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium Chloride2×HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 666435331-trityl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 666434571-trityl-1H-pyrazolo[3,4-b]pyridine-4-carboxamideYield 77.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 1-tritylpyrazolo[5,4-b]pyridine-4-carboxylic acid (3.996 g, 9.856 mmol) in DMF (70.01 mL) was treated sequentially with triethylamine (2.194 g, 3.022 mL, 21.68 mmol), ammonium chloride (2.636 g, 1.723 mL, 49.28 mmol) and TBTU (4.746 g, 14.78 mmol) at RT under nitrogen. The reaction was allowed to stir for 4 hours and then treated with DCM and saturated aqueous NH4Cl. The aqueous was extracted twice with DCM and the organic layer washed with aqueous NH4Cl, followed by 0.5M NaOH, dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography (70:9:1 DCM/MeOH/NH4OH) to give the product as white solid (3.08 g, 77% Yield). 1H NMR (DMSO, 400 MHz) δ 7.18-7.29 (15H, m), 7.44 (1H, m), 7.83 (1H, br s), 8.27 (1H, br s), 8.37 (1H, m), 8.46 (1H, m); MS (ES+) 405.12

Workup

  1. extractionThe aqueous was extracted twice with DCM
  2. washthe organic layer washed with aqueous NH4Cl
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (70:9:1 DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-24e3760cf6e7494b90c307ad4187279e
Source dataset
uspto-grants-2013_09
Patent number
US08541445B2

Reaction notes

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