Morpholine → 7-Chloro-thieno[3,2-b]pyridin-2-yl-morpholin-4-yl-methanone

HRID 1013643Notes

Reaction equation

HRID 1013643 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O-:13])=O)[S:10][C:3]=12.[Li+].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(N(C(C)C)C(C)C)C>C(Cl)Cl.CN(C=O)C.C(Cl)(=O)C(Cl)=O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[O:13])[S:10][C:3]=12

Participants

7

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 23677819Lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate

Product 1

HCID 222786227-Chloro-thieno[3,2-b]pyridin-2-yl-morpholin-4-yl-methanone

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 65578Oxalyl chlorideSolvent

Procedure

[Lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate (100 mg, 455 μmol) was dissolved in CH2Cl2(5 mL) with one drop of DMF and oxalyl chloride (2 mL) was added. The mixture was stirred at RT for one hour then concentrated and dried under high vacuum. Morpholine (60 μl, 683 μmol) was then added to the mixture with N-ethyl-N-isopropylpropan-2-amine (238 μl, 1366 μmol) and the mixture was stirred for 20 hours. The mix was then concentrated and purified using 0 to 100% 90/10/1 CH2Cl2/MeOH/ammonium hydroxide in CH2Cl2 to afford (7-chlorothieno[3,2-b]pyridin-2-yl)(morpholino)methanone.

Workup

  1. additionwas added
  2. concentrationthen concentrated
  3. customdried under high vacuum
  4. stirringthe mixture was stirred for 20 hours
  5. concentrationThe mix was then concentrated
  6. custompurified

Sources & evidence

ORD record
ord-98cefc0c92a647839256b7b15500246d
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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