Triethylamine → Ethyl 2-(3-Fluoro-4-(2-(3-methoxy-4-(2-morpholinoethoxy)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenylamino)-2-oxoacetate

HRID 418646Notes

Reaction equation

HRID 418646 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][C:16]=1[O:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]2[CH:24]=[C:25]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)=[C:29]([O:42][CH3:43])[CH:28]=3)[S:26][C:19]=12)[NH2:13].C(N(CC)CC)C>ClCCl>[F:9][C:10]1[CH:11]=[C:12]([NH:13][C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:14]=[CH:15][C:16]=1[O:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]2[CH:24]=[C:25]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]4[CH2:37][CH2:38][O:39][CH2:40][CH2:41]4)=[C:29]([O:42][CH3:43])[CH:28]=3)[S:26][C:19]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 587902763-Fluoro-4-(2-(3-methoxy-4-(2-morpholinoethoxy)phenyl)thieno[3,2-b]pyridin-7-yloxy)aniline

Product 1

HCID 58790158Ethyl 2-(3-Fluoro-4-(2-(3-methoxy-4-(2-morpholinoethoxy)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenylamino)-2-oxoacetateYield 47.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (0.11 mL, 0.95 mmol) was added to a solution of the amine 139 (313 mg, 0.63 mmol) and triethylamine (0.18 mL, 1.26 mmol) in dichloromethane (16 mL). The reaction mixture was stirred at room temperature until completion of the reaction. The mixture was quenched with a saturated aqueous solution of ammonium chloride and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and evaporated. The crude product was purified by flash chromatography (eluent: 5% MeOH/95% DCM to 7% MeOH/93% DCM) to afford title compound 140 as a yellow solid (178 mg, 47% yield). MS (m/z): 596.1 (M+H).

Workup

  1. customThe mixture was quenched with a saturated aqueous solution of ammonium chloride
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography (eluent: 5% MeOH/95% DCM to 7% MeOH/93% DCM)

Sources & evidence

ORD record
ord-0bd2555af1894925b7ff3acc3ed3d8d5
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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