Ethyl 1-cyclopropyl-7-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenylethynyl]-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylate → ethyl (Z)-7-[2-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenyl]-vinyl]-1-cyclopropyl-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylate

HRID 963435Notes

Reaction equation

HRID 963435 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:36])=[C:11]([C:15]#[C:16][C:17]4[CH:22]=[C:21]([CH2:23][C:24]5[C:25]([NH2:31])=[N:26][C:27]([NH2:30])=[N:28][CH:29]=5)[CH:20]=[C:19]([O:32][CH3:33])[C:18]=4[O:34][CH3:35])[C:12]=3[F:14])[C:7](=[O:37])[C:6]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:5]2)[CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[NH2:30][C:27]1[N:26]=[C:25]([NH2:31])[C:24]([CH2:23][C:21]2[CH:20]=[C:19]([O:32][CH3:33])[C:18]([O:34][CH3:35])=[C:17](/[CH:16]=[CH:15]\[C:11]3[C:12]([F:14])=[C:13]4[C:8]([C:7](=[O:37])[C:6]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:5][N:4]4[CH:1]4[CH2:3][CH2:2]4)=[CH:9][C:10]=3[F:36])[CH:22]=2)=[CH:29][N:28]=1

Participants

5

Reactant 2

HCID 19081771Ethyl 1-cyclopropyl-7-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenylethynyl]-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86752727ethyl (Z)-7-[2-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenyl]-vinyl]-1-cyclopropyl-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylateYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 250 mg of ethyl 1-cyclopropyl-7-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenylethynyl]-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylate (Example 12a)) and 50 mg of 5% palladium-on-charcoal in 50 ml of methanol is hydrogenated at normal hydrogen pressure. The reaction mixture is filtered after 6 hrs. The filtrate is concentrated and the crude product is triturated in succession with 20 ml and 10 ml of ethyl acetate and filtered off under suction. 133 mg (53%) of ethyl (Z)-7-[2-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenyl]-vinyl]-1-cyclopropyl-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylate are obtained as a colourless solid. M.p.>220°. Mass spectrum: peaks: inter alia at 577 (M+, 100%), 562 (35%), 530 (28%), 516 (68%), 474 (45%).

Workup

  1. filtrationThe reaction mixture is filtered after 6 hrs
  2. concentrationThe filtrate is concentrated
  3. customthe crude product is triturated in succession with 20 ml and 10 ml of ethyl acetate
  4. filtrationfiltered off under suction

Sources & evidence

ORD record
ord-11da8ed0ce0644c2a0c3fea076535956
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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