Triethylamine → HCID 68857974, compound

HRID 491261Notes

Reaction equation

HRID 491261 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5]N=1.[Cl:12][C:13]1[C:21]2[C:20]([NH:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)=[N:19][CH:18]=[N:17][C:16]=2[S:15][CH:14]=1.[CH3:32]CN(CC)CC>C(Cl)Cl>[Cl:12][C:13]1[C:21]2[C:20]([NH:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][C:7](=[O:8])[C:6]4[CH:5]=[CH:32][C:3]([O:2][CH3:1])=[CH:11][CH:10]=4)=[CH:27][CH:26]=3)=[N:19][CH:18]=[N:17][C:16]=2[S:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 178629506-Methoxypyridine-3-carbonyl chlorideHCID 67309598HCID 67309598, compound

Product 1

HCID 68857974HCID 68857974, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 6-methoxynicotinoyl chloride (343 mg, 2 mmol) in CH2Cl2 (5 mL) was added dropwise to a solution of 4-{2-[(5-chlorothieno[2,3-d]pyrimidin-4-yl)amino]ethyl}phenol (611 mg, 2 mmol) and Et3N (1.0g, 10 mmol) in CH2Cl2 (5 mL) and the solution was stirred at room temperature overnight. The reaction was diluted with CH2Cl2 (20 mL) and washed with H2O, 1M NaOH, and brine. The organics were dried (Na2SO4) and filtered through silica gel. The solvent was stripped yielding 200 mg of material which was purified via HPLC giving 48mg, 0.11 mmol, 5 percent yield.

Workup

  1. washwashed with H2O, 1M NaOH, and brine
  2. dry with materialThe organics were dried (Na2SO4)
  3. filtrationfiltered through silica gel

Sources & evidence

ORD record
ord-3c24f56d45214d68b746b9ca54aff457
Source dataset
uspto-grants-2009_05
Patent number
US07531482B2

Reaction notes

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