Hydrochloric Acid → 1-(3-(5-(3-(2-Methylpyridin-3-yloxy)-5-(trifluoromethyl)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)ethanone hydrochloride

HRID 1809621노트

반응식

HRID 1809621 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]([C:29]([F:32])([F:31])[F:30])=[CH:17][N:16]=3)[S:11][N:10]=1)[CH2:2]2.C(N(CC)CC)C.[C:40](OC(=O)C)(=[O:42])[CH3:41].[ClH:47]>C(Cl)Cl>[ClH:47].[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[CH2:2][CH:1]5[N:8]([C:40](=[O:42])[CH3:41])[CH:5]([CH2:6][CH2:7]5)[CH2:4]4)[N:13]=3)=[N:16][CH:17]=[C:18]([C:29]([F:30])([F:31])[F:32])[CH:19]=2)=[CH:27][CH:26]=[CH:25][N:24]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67487542HCID 67487542, 화합물

생성물 1

HCID 687079401-(3-(5-(3-(2-Methylpyridin-3-yloxy)-5-(trifluoromethyl)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)ethanone hydrochloride수율 47.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-(8-azabicyclo[3.2.1]octan-3-yl)-N-(3-(2-methylpyridin-3-yloxy)-5-(trifluoromethyl)pyridin-2-yl)-1,2,4-thiadiazol-5-amine (45 mg, 0.0973 mmol) was dissolved in CH2Cl2 (2 mL) and triethylamine (67.8 μL, 0.486 mmol) and acetic anhydride (13.8 μL, 0.146 mmol) were added. After 10 minutes the reaction was partitioned between saturated aqueous NaHCO3 and CH2Cl2, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (10% methanol in EtOAc) to afford 1-(3-(5-(3-(2-methylpyridin-3-yloxy)-5-(trifluoromethyl)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)ethanone hydrochloride (25 mg, 0.0462 mmol, 47.5% yield) as a solid after HCl salt formation. Mass spectrum (apci) m/z=505.2 (M+H—HCl).

후처리

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

출처 및 근거

ORD 기록
ord-be30ab94e6dc4e67bec14a85ed9a277f
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362037B2

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