6-Aminoquinoline → 2-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid quinolin-6-ylamide

HRID 1773626Notes

Reaction equation

HRID 1773626 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([C:11]([OH:13])=O)[C:6]=2[N:7]=1.[N:14]1[C:23]2[C:18](=[CH:19][C:20]([NH2:24])=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.C(N(CC)C(C)C)(C)C.C1CN(C(ON2N=NC3C2=CC=CC=3)=[N+]2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl.O.CN(C)C=O>[N:14]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:11]([C:8]3[C:6]4[N:7]=[C:2]([Cl:1])[N:3]=[CH:4][C:5]=4[S:10][CH:9]=3)=[O:13])=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 113736-AminoquinolineHCID 81531DiisopropylethylamineHCID 13685355O-(Benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylene)uronium HexafluorophosphateHCID 580563052-Chlorothieno[3,2-D]pyrimidine-7-carboxylic acid

Product 1

HCID 866613802-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid quinolin-6-ylamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.050 g (0.233 mmole) 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid, 0.0672 g (0.466 mmole) of quinolin-6-amine, 0.122 mL (0.699 mmole) of N,N-diisopropylethylamine and 1.55 mL of dimethylformamide was added 0.111 g (0.256 mmole) of O-(benzotriazol-1-yl)-N,N,N′,N′-bis(tetramethylene)uronium hexafluorophosphate. The mixture was stirred at room temperature for 2 hours. Water and dichloromethane were added. The aqueous layer was washed three times with dichloromethane. The combined organic layer was washed with aqueous sodium carbonate, brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was dried in high vacuum to give 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid quinolin-6-ylamide as a yellow-greenish solid

Workup

  1. washThe aqueous layer was washed three times with dichloromethane
  2. washThe combined organic layer was washed with aqueous sodium carbonate, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was dried in high vacuum

Sources & evidence

ORD record
ord-fc77dd1508e84bb18f42cc8477ec4470
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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