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Oxalyl chloride → 1,3-Dimethyl-4-[2-[[(E)-4,4,4-trifluorobut-2-enoyl]amino]ethylamino]pyrazolo-[3,4-b]-pyridine-5-carboxamide

HRID 333092
Notes
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Reaction equation

HRID 333092 reaction equation
[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.FC(F)(F)S(O)(=O)=O.[NH2:24][CH2:25][CH2:26][NH:27][C:28]1[C:33]([C:34]([NH2:36])=[O:35])=[CH:32][N:31]=[C:30]2[N:37]([CH3:41])[N:38]=[C:39]([CH3:40])[C:29]=12.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C)C=O>[CH3:41][N:37]1[C:30]2=[N:31][CH:32]=[C:33]([C:34]([NH2:36])=[O:35])[C:28]([NH:27][CH2:26][CH2:25][NH:24][C:5](=[O:6])/[CH:4]=[CH:3]/[C:2]([F:9])([F:8])[F:1])=[C:29]2[C:39]([CH3:40])=[N:38]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 57096144,4,4-Trifluorocrotonic acidHCID 866911764-(2-Aminoethylamino)-1,3-dimethyl-pyrazolo[3,4-b]pyridine-5-carboxamide trifluoromethanesulfonate

Product 1

HCID 680947861,3-Dimethyl-4-[2-[[(E)-4,4,4-trifluorobut-2-enoyl]amino]ethylamino]pyrazolo-[3,4-b]-pyridine-5-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneCatalystHCID 6228DimethylformamideSolvent

Procedure

(E)-4,4,4-Trifluorobut-2-enoic acid (21 mg, 0.15 mmol) was dissolved in DCM (2 ml containing one drop of dimethyl formamide), oxalyl chloride was added (19 mg, 0.15 mmol) and the solution was stirred at room temperature for 15 minutes. This solution was added to a solution of 4-(2-aminoethylamino)-1,3-dimethyl-pyrazolo[3,4-b]pyridine-5-carboxamide trifluoromethanesulfonate (40 mg, 0.1 mmol) and diisopropylethylamine (60 μl, 0.35 mmol) dissolved in dimethylformamide (1 ml) and the resulting mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure and the residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 2.1 mg (0.005 mmol, 5.7%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  4. customto yield 2.1 mg (0.005 mmol, 5.7%)

Sources & evidence

ORD record
ord-0387af41db0544c5ac5486a642657c71
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08877934B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes