Triethylamine → Thieno[2,3-b]pyridine-5-carboxylic acid (5-phenoxy-thiophen-2-ylmethyl)-amide

HRID 2080258Notes

Reaction equation

HRID 2080258 reaction equation
[Li].[S:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([OH:13])=O)[CH:10]=[C:5]2[CH:4]=[CH:3]1.[O:14]([C:21]1[S:25][C:24]([CH2:26][NH2:27])=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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>[O:14]([C:21]1[S:25][C:24]([CH2:26][NH:27][C:11]([C:9]2[CH:10]=[C:5]3[CH:4]=[CH:3][S:2][C:6]3=[N:7][CH:8]=2)=[O:13])=[CH:23][CH:22]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 3028194LithiumHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 14025921Thieno[2,3-b]pyridine-5-carboxylic acidHCID 23130515C-(5-Phenoxy thiophen-2-yl)methylamine

Product 1

HCID 58388082Thieno[2,3-b]pyridine-5-carboxylic acid (5-phenoxy-thiophen-2-ylmethyl)-amideYield 40%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Then, the lithium salt of the resulting thieno[2,3-b]pyridine-5-carboxylic acid, C-(5-phenoxy-thiophen-2-yl)-methylamine described in Preparation Example 26 (4.7 mg, 23 μmol), benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (14 mg, 32 μmol) and triethylamine (9 μl, 63 μmol) were dissolved in N,N-dimethylformamide (0.5 mL), and the solution was stirred at room temperature for 2 hours. Water and ethyl acetate were added to the reaction solution, the organic layer was partitioned, and washed with brine. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1), and the title compound (3.0 mg, 8.2 μmol, 40%) was obtained as a white solid.

Workup

  1. customthe organic layer was partitioned
  2. washwashed with brine
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-fe34dbaf75b6427caf637a2964197771
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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