Hydrochloric Acid → HCID 67487736, 화합물

HRID 1809623노트

반응식

HRID 1809623 반응식
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]([C:9]1[N:13]=[C:12]([NH:14][C:15]3[C:20]([O:21][C:22]4[C:23]([CH3:28])=[N:24][CH:25]=[CH:26][CH:27]=4)=[CH:19][C:18]([S:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=4)=[CH:17][N:16]=3)[S:11][N:10]=1)[CH2:2]2.C(N(CC)CC)C.[C:43](OC(=O)C)(=[O:45])[CH3:44].[ClH:50]>C(Cl)Cl>[ClH:50].[CH3:28][C:23]1[C:22]([O:21][C:20]2[C:15]([NH:14][C:12]3[S:11][N:10]=[C:9]([CH:3]4[CH2:4][CH:5]5[N:8]([C:43](=[O:45])[CH3:44])[CH:1]([CH2:7][CH2:6]5)[CH2:2]4)[N:13]=3)=[N:16][CH:17]=[C:18]([S:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)[CH:19]=2)=[CH:27][CH:26]=[CH:25][N:24]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67487214HCID 67487214, 화합물

생성물 1

HCID 67487736HCID 67487736, 화합물수율 82.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-(8-azabicyclo[3.2.1]octan-3-yl)-N-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-yl)-1,2,4-thiadiazol-5-amine (100 mg, 0.199 mmol) was dissolved in CH2Cl2 (3 mL) and triethylamine (41.5 μL, 0.298 mmol) and acetic anhydride (22.5 μL, 0.238 mmol) were added and the reaction stirred for 5 minutes. The reaction was partitioned between saturated aqueous NaHCO3 and CH2Cl2, dried over sodium sulfate, filtered, concentrated and purified on silica gel (10% methanol in EtOAc) to afford 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 (95.2 mg, 0.164 mmol, 82.4% yield) as a solid after HCl salt formation. Mass spectrum (apci) m/z=546.0 (M+H—HCl).

후처리

  1. customThe reaction was partitioned between saturated aqueous NaHCO3 and CH2Cl2
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on silica gel (10% methanol in EtOAc)

출처 및 근거

ORD 기록
ord-c6759183c9c94bd7959e0eb14d4a15d4
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362037B2

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