Hydrochloric Acid → HCID 67486992, 화합물

HRID 1809629노트

반응식

HRID 1809629 반응식
C([O:4][CH2:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([C:16]1[N:20]=[C:19]([NH:21][C:22]3[C:27]([O:28][C:29]4[C:30]([CH3:35])=[N:31][CH:32]=[CH:33][CH:34]=4)=[CH:26][C:25]([S:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=4)=[CH:24][N:23]=3)[S:18][N:17]=1)[CH2:12]2)=[O:7])(=O)C.C([O-])([O-])=O.[K+].[K+].[ClH:49]>CCO>[ClH:49].[OH:4][CH2:5][C:6]([N:8]1[CH:9]2[CH2:15][CH2:14][CH:13]1[CH2:12][CH:11]([C:16]1[N:20]=[C:19]([NH:21][C:22]3[C:27]([O:28][C:29]4[C:30]([CH3:35])=[N:31][CH:32]=[CH:33][CH:34]=4)=[CH:26][C:25]([S:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=4)=[CH:24][N:23]=3)[S:18][N:17]=1)[CH2:10]2)=[O:7]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67487819HCID 67487819, 화합물

생성물 1

HCID 67486992HCID 67486992, 화합물수율 83.1%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
50 °C

실험 절차

2-(3-(5-(3-(2-Methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)-2-oxoethyl acetate (95 mg, 0.157 mmol) was dissolved in EtOH (3 mL) and K2CO3 (excess) was added and heated to 50° C. for 1.5 hr. The reaction was partitioned between CH2Cl2 and saturated aqueous NH4Cl, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (15% methanol in EtOAc) to afford 2-hydroxy-1-(3-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)ethanone hydrochloride (78.2 mg, 0.131 mmol, 83.1% yield) as a solid after HCl salt formation. Mass spectrum (apci) m/z=562.2 (M+H—HCl).

후처리

  1. customThe reaction was partitioned between CH2Cl2 and saturated aqueous NH4Cl
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel (15% methanol in EtOAc)

출처 및 근거

ORD 기록
ord-c829149fdb044caaa6f814f3800a3e12
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362037B2

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