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

HRID 1740080노트

반응식

HRID 1740080 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ca3d266cc1e145bcab3038d715142d62
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968967

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