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Oxalyl chloride → (E)-4,4,4-Trifluoro-N-[2-(furo[3,2-b]pyridin-7-ylamino)-2-oxo-ethyl]but-2-enamide

HRID 333087
Notes
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Reaction equation

HRID 333087 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.Cl.[NH2:17][CH2:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[CH:28]=[CH:29][O:30][C:23]=12)=[O:20].C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C)C=O>[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5]([NH:17][CH2:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[CH:28]=[CH:29][O:30][C:23]=12)=[O:20])=[O:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 57096144,4,4-Trifluorocrotonic acidHCID 668353512-Amino-N-furo[3,2-b]pyridin-7-yl-acetamide hydrochloride

Product 1

HCID 56947336(E)-4,4,4-Trifluoro-N-[2-(furo[3,2-b]pyridin-7-ylamino)-2-oxo-ethyl]but-2-enamide

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

(E)-4,4,4-Trifluorobut-2-enoic acid (15.4 mg, 0.11 mmol) was dissolved in DCM (0.75 ml containing one drop of dimethyl formamide), oxalyl chloride was added (14 mg, 0.11 mmol) and the solution was stirred at room temperature for 15 minutes. This solution was added to a solution of 2-amino-N-furo[3,2-b]pyridin-7-yl-acetamide hydrochloride (25.3 mg, 0.11 mmol) and diisopropylethylamine (44 μl, 0.25 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 6.9 mg (0.022 mmol, 20%).

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 6.9 mg (0.022 mmol, 20%)

Sources & evidence

ORD record
ord-e2c379de5d714d4094c86493a3900f9a
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