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 1809621ノート

反応式

HRID 1809621 の反応式
[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

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67487542HCID 67487542、化合物

生成物 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 hydrochloride収率 47.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-be30ab94e6dc4e67bec14a85ed9a277f
出典データセット
uspto-grants-2013_01
特許番号
US08362037B2

反応ノート

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