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Potassium Carbonate → 1-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methoxyisoquinoline-3-carboxylic acid

HRID 2234023
ノート
印刷プレビュー

反応式

HRID 2234023 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[C:4]([C:14]([O:16]CC)=[O:15])[N:3]=1.FC(F)(F)C([O-])=O.[Cl:26][C:27]1[C:31]([Cl:32])=[C:30]([CH3:33])[NH:29][C:28]=1[C:34]([NH:36][CH:37]1[CH2:42][CH2:41][NH2+:40][CH2:39][CH2:38]1)=[O:35].C([O-])([O-])=O.[K+].[K+]>C(O)(C)(C)C>[Cl:26][C:27]1[C:31]([Cl:32])=[C:30]([CH3:33])[NH:29][C:28]=1[C:34]([NH:36][CH:37]1[CH2:42][CH2:41][N:40]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([O:12][CH3:13])=[C:4]([C:14]([OH:16])=[O:15])[N:3]=2)[CH2:39][CH2:38]1)=[O:35]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 685798674-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidinium trifluoroacetate2 回HCID 86038348Ethyl 1-chloro-4-methoxyisoquinoline-3-carboxylate

生成物 1

HCID 685794921-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methoxyisoquinoline-3-carboxylic acid収率 1.8%

試薬・触媒・溶媒 1

HCID 6386
tert-Butanol
溶媒

反応条件

温度
170 °C

実験手順

In a sealed high pressure container with a Teflon lining was combined ethyl 1-chloro-4-methoxyisoquinoline-3-carboxylate (EP 650961 A1; 390 mg, 1.55 mmol), 4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidinium trifluoroacetate (Intermediate 86; 1.7 g, 4.4 mmol), and K2CO3 (2.2 g) in 20 ml tert-butanol. The container was heated at 170° C. with stirring for 8 hours. The solution was concentrated by rotary evaporation and reconstituted with EtOAc. The organic layer was washed 4× with H2O, and dried over MgSO4. Crude ethyl 1-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methoxyisoquinoline-3-carboxylate was purified by reverse phase Si yielding 20 mg of the intermediate ester. The ethyl ester was then hydrolyzed as in Example 262 to yield 13.5 mg white solid final product.

後処理

  1. concentrationThe solution was concentrated by rotary evaporation
  2. washThe organic layer was washed 4× with H2O
  3. dry with materialdried over MgSO4
  4. customCrude ethyl 1-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methoxyisoquinoline-3-carboxylate was purified by reverse phase Si yielding 20 mg of the intermediate ester

出典と根拠

ORDレコード
ord-4da3fb760a3945d2990f2f5807e3a7b5
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07709503B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート