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Triethylamine → Imidazo[1,2-a]pyridine-6-carboxamide,n-[[5-(3-fluorophenoxy)-2-thienyl]methyl]-

HRID 2080006
Notes
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Reaction equation

HRID 2080006 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[CH:6][C:5]=12.[F:13][C:14]1[CH:15]=[C:16]([CH:25]=[CH:26][CH:27]=1)[O:17][C:18]1[S:22][C:21]([CH2:23][NH2:24])=[CH:20][CH:19]=1.F[P-](F)(F)(F)(F)F.N1([P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.O>[F:13][C:14]1[CH:15]=[C:16]([CH:25]=[CH:26][CH:27]=1)[O:17][C:18]1[S:22][C:21]([CH2:23][NH:24][C:10]([C:8]2[CH:7]=[CH:6][C:5]3[N:4]([CH:3]=[CH:2][N:1]=3)[CH:9]=2)=[O:12])=[CH:20][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 7075376Imidazo(1,2-a)pyridine-6-carboxylic acidHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 23130606C-(5-(3-fluorophenoxy)thiophen-2-yl)methylamine

Product 1

HCID 58387866Imidazo[1,2-a]pyridine-6-carboxamide,n-[[5-(3-fluorophenoxy)-2-thienyl]methyl]-Yield 46.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent3×

Conditions

Temperature
80 °C

Procedure

To a solution of imidazo[1,2-a]pyridine-6-carboxylic acid (87 mg, 0.54 mmol) and C-(5-(3-fluorophenoxy)thiophen-2-yl)methylamine (120 mg, 0.54 mmol) in N,N-dimethylformamide (5 mL) were added benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (240 mg, 0.54 mmol) and triethylamine(0.15 mL, 1.08 mmol), and the solution was stirred for 40 minutes at 80° C. Water and ethyl acetate were added to the reaction mixture for extraction, and the organic layer was washed twice with water. Silica gel was added to the organic layer, solvent was evaporated in vacuo for adsorption, purification was carried out by silica gel column chromatography (hexane:ethyl acetate=1:1, then ethyl acetate), and the title compound (90 mg, 0.25 mmol, 45.4%) was obtained as a light brown oil.

Workup

  1. washthe organic layer was washed twice with water
  2. additionSilica gel was added to the organic layer, solvent
  3. customwas evaporated in vacuo for adsorption, purification

Sources & evidence

ORD record
ord-336412bd8be14347a47b206ea71aa70e
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07932272B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes