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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 963435
ノート
印刷プレビュー

反応式

HRID 963435 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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、化合物

生成物 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-carboxylate収率 53%

試薬・触媒・溶媒 2

HCID 23938Palladium
触媒
HCID 887Methanol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-11da8ed0ce0644c2a0c3fea076535956
出典データセット
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05763450

反応ノート

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