Hydrochloric Acid → 1-(4-Amidinophenyl)-3-(4-t-butylphenyl)-4-{[4-(ethoxycarbonylmethyloxy)-1-piperidinyl]carbonyl}-2-methyl-2H-pyrazol-5-one monohydrochloride

HRID 1740080ノート

反応式

HRID 1740080 の反応式
[ClH:1].[C:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]([CH3:41])[N:14]([C:33]3[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=3)[C:15](=[O:32])[C:16]=2[C:17]([N:19]2[CH2:24][CH2:23][CH:22]([O:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:21][CH2:20]2)=[O:18])=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].C(=O)([O-])[O-].[NH4+:46].[NH4+]>C(O)C>[ClH:1].[C:39]([C:36]1[CH:35]=[CH:34][C:33]([N:14]2[C:15](=[O:32])[C:16]([C:17]([N:19]3[CH2:20][CH2:21][CH:22]([O:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:24]3)=[O:18])=[C:12]([C:9]3[CH:8]=[CH:7][C:6]([C:2]([CH3:3])([CH3:4])[CH3:5])=[CH:11][CH:10]=3)[N:13]2[CH3:41])=[CH:38][CH:37]=1)(=[NH:46])[NH2:40]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 517111Ammonium CarbonateHCID 154355023-(4-t-Butylphenyl)-4-{[4-(ethoxycarbonylmethyloxy)-1-piperidinyl]carbonyl}-1-(4-cyanophenyl)-2-methyl-2H-pyrazol-5-one

生成物 1

HCID 218376491-(4-Amidinophenyl)-3-(4-t-butylphenyl)-4-{[4-(ethoxycarbonylmethyloxy)-1-piperidinyl]carbonyl}-2-methyl-2H-pyrazol-5-one monohydrochloride

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Dry hydrogen chloride was introduced into a mixture of 1.19 g of 3-(4-t-butylphenyl)-4-{[4-(ethoxycarbonylmethyloxy)-1-piperidinyl]carbonyl}-1-(4-cyanophenyl)-2-methyl-2H-pyrazol-5-one and 15 ml of absolute ethanol under cooling with ice for 2 hours, and the mixture was stirred under cooling with ice for another 15 hours. 38.5 g of ammonium carbonate was added to adjust the pH to 7-8, and the reaction solution was stirred at room temperature for 22 hours. The precipitated insolubles were filtered off, and hydrochloric acid in ethanol was added to the mother liquor to adjust the pH to 3. The precipitated crystals were filtered off, and the mother liquor was concentrated under reduced pressure. The residue was purified by C-18 reverse phase silica gel chromatography (water/methanol=2:1). The resulting crude crystals were recrystallized in methanol-chloroform-ethyl acetate to give 543 mg of the title compound as colorless crystals.

後処理

  1. temperatureunder cooling with ice for 2 hours
  2. temperatureunder cooling with ice for another 15 hours
  3. stirringthe reaction solution was stirred at room temperature for 22 hours
  4. filtrationThe precipitated insolubles were filtered off
  5. additionhydrochloric acid in ethanol was added to the mother liquor
  6. filtrationThe precipitated crystals were filtered off
  7. concentrationthe mother liquor was concentrated under reduced pressure
  8. customThe residue was purified by C-18 reverse phase silica gel chromatography (water/methanol=2:1)
  9. customThe resulting crude crystals were recrystallized in methanol-chloroform-ethyl acetate

出典と根拠

ORDレコード
ord-ca3d266cc1e145bcab3038d715142d62
出典データセット
uspto-grants-1999_10
特許番号
US05968967

反応ノート

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