Triethylamine → Imidazo[1,2-a]pyridine-6-carboxylic acid (5-(3-chloro-phenoxy)-thiophen-2-ylmethyl)-amide

HRID 2080255Notes

Reaction equation

HRID 2080255 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[S:10][C:9]([CH2:11][NH2:12])=[CH:8][CH:7]=1.[N:16]1[CH:17]=[CH:18][N:19]2[CH:24]=[C:23]([C:25](O)=[O:26])[CH:22]=[CH:21][C:20]=12.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[S:10][C:9]([CH2:11][NH:12][C:25]([C:23]2[CH:22]=[CH:21][C:20]3[N:19]([CH:18]=[CH:17][N:16]=3)[CH:24]=2)=[O:26])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7075376Imidazo(1,2-a)pyridine-6-carboxylic acidHCID 23130411C-(5-(3-chloro-phenoxy)-thiophen-2-yl)-methylamine

Product 1

HCID 58388057Imidazo[1,2-a]pyridine-6-carboxylic acid (5-(3-chloro-phenoxy)-thiophen-2-ylmethyl)-amideYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of C-(5-(3-chloro-phenoxy)-thiophen-2-yl)-methylamine described in Preparation Example 167 (104 mg, 0.434 mmol) and imidazo[1,2-a]pyridine-6-carboxylic acid (77 mg, 0.477 mmol) in N,N-dimethylformamide (3 mL) were added benzotriazol-1-yloxy tris(dimethylamino)phosphonium hexafluorophosphate (250 mg, 0.564 mmol) and triethylamine (181 μL) at room temperature, and the solution was stirred at room temperature for 4 hours. Water was added to the reaction solution, which was then extracted with ethyl acetate, and the organic layer was washed with water and brine. Anhydrous magnesium sulfate was added to the organic layer for drying, filtration was carried out, then, the solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (ethyl acetate/methanol=40/1), and the title compound (149 mg, 89%) was obtained as a white solid.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washthe organic layer was washed with water and brine
  3. additionAnhydrous magnesium sulfate was added to the organic layer
  4. customfor drying
  5. filtrationfiltration
  6. customthe solvent was evaporated in vacuo
  7. customthe residue was purified by NH silica gel column chromatography (ethyl acetate/methanol=40/1)

Sources & evidence

ORD record
ord-acf750ea5c1447968b379fa3692dce42
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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