Hydrochloric Acid → HCID 67487736、化合物

HRID 1809623ノート

反応式

HRID 1809623 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]([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

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67487214HCID 67487214、化合物

生成物 1

HCID 67487736HCID 67487736、化合物収率 82.4%

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-(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).

後処理

  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)

出典と根拠

ORDレコード
ord-c6759183c9c94bd7959e0eb14d4a15d4
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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