Hydrochloric Acid → 1-{4-[4-(9-Oxa-3,7-diazabicyclo[3.3.1]non-3-yl)-1-(2,2,2-trifluoroethyl)-1h-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}-3-pyridin-4-ylurea

HRID 1093201노트

반응식

HRID 1093201 반응식
Cl.[N:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:47])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:22]=[C:21]4[N:23]([CH2:26][C:27]([F:30])([F:29])[F:28])[N:24]=[CH:25][C:20]4=[C:19]([N:31]4[CH2:38][CH:37]5[O:39][CH:33]([CH2:34][N:35](C(OC(C)(C)C)=O)[CH2:36]5)[CH2:32]4)[N:18]=3)=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.Cl>ClCCl.CO.O1CCOCC1>[CH:33]12[O:39][CH:37]([CH2:36][NH:35][CH2:34]1)[CH2:38][N:31]([C:19]1[N:18]=[C:17]([C:14]3[CH:13]=[CH:12][C:11]([NH:10][C:9]([NH:8][C:5]4[CH:4]=[CH:3][N:2]=[CH:7][CH:6]=4)=[O:47])=[CH:16][CH:15]=3)[N:22]=[C:21]3[N:23]([CH2:26][C:27]([F:29])([F:30])[F:28])[N:24]=[CH:25][C:20]=13)[CH2:32]2

참가 물질

6

반응물 2

HCID 313Hydrochloric AcidHCID 66588973Tert-butyl 7-(6-(4-(3-pyridin-4-ylureido)phenyl)-1-(2,2,2-trifluoroethyl)-1h-pyrazolo[3,4-d]pyrimidin-4-yl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate.hydrochloride

생성물 1

HCID 574246031-{4-[4-(9-Oxa-3,7-diazabicyclo[3.3.1]non-3-yl)-1-(2,2,2-trifluoroethyl)-1h-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}-3-pyridin-4-ylurea

시약·촉매·용매 3

HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

Tert-butyl 7-(6-(4-(3-pyridin-4-ylureido)phenyl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate.hydrochloride (256 mg, 0.38 mmol) was dissolved in dichloromethane (20 mL) with the aid of a minimum volume of methanol. The solution was treated with 4 N hydrogen chloride in dioxane (2 mL), which caused the precipitation of a white solid within 10 minutes. The solid was collected by Buchner filtration, washed with methanol, and dried under house vacuum. A portion of the crude solid (assumed dihydrochloride) was purified by reverse-phase high performance liquid chromatography using a Phenomenex Prodigy 21 mm×250 mm column, running a gradient elution of 5% acetonitrile/95% of 0.1% aqueous trifluoroacetic acid to 65% acetonitrile to provide 1-{4-[4-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}-3-pyridin-4-ylurea.2TFA (22 mg). MS (ES+): 540.2 (M+H)+

후처리

  1. customthe precipitation of a white solid within 10 minutes
  2. filtrationThe solid was collected by Buchner filtration
  3. washwashed with methanol
  4. customdried under house vacuum
  5. customA portion of the crude solid (assumed dihydrochloride) was purified by reverse-phase high performance liquid chromatography
  6. washa gradient elution of 5% acetonitrile/95% of 0.1% aqueous trifluoroacetic acid to 65% acetonitrile

출처 및 근거

ORD 기록
ord-0fdf995b6cf3424c9633d3f7549eadd7
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129371B2

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