Potassium Carbonate → (S)-N-(5-((3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl)methyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

HRID 43005

反応式

HRID 43005 の反応式
O[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@H:7]([NH:12][S:13]([CH:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])[CH2:6]2.S(Cl)(Cl)=O.[F:23][C:24]([F:35])([F:34])[C:25]1[C:33]2[CH2:32][CH2:31][CH2:30][CH2:29][C:28]=2[NH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[F:35][C:24]([F:23])([F:34])[C:25]1[C:33]2[CH2:32][CH2:31][CH2:30][CH2:29][C:28]=2[N:27]([CH2:2][C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[CH2:8][C@H:7]([NH:12][S:13]([CH:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])[CH2:6]3)[N:26]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 28028633-(Trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazoleHCID 67088215(S)-N-(5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

生成物 1

HCID 53323974(S)-N-(5-((3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl)methyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide収率 3.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(S)—N-(5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide (23 mg, 0.086 mmol) was dissolved in DCM (5 mL) and thionyl chloride (51 mg, 0.43 mmol) was added. The reaction mixture was stirred at room temperature for 1 h before being concentrated to dryness. The whole was dissolved in DMF (2 mL) to this was added 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (25 mg, 0.086 mmol) followed by potassium carbonate (24 mg, 0.172 mmol). The reaction mixture was heated to 65° C. for 3 h before being quenched with water (2 mL) and the organics extracted with EtOAc (3×5 mL). The combined organics were washed with brine, dried (MgSO4) and concentrated under reduced pressure. Purification by preparative basic HPLC gave the title compound (1.2 mg, 2.7 μmol, 2.9%). MS (ESI): m/z [M+H]+ 442.2

後処理

  1. concentrationbefore being concentrated to dryness
  2. dissolutionThe whole was dissolved in DMF (2 mL) to
  3. temperatureThe reaction mixture was heated to 65° C. for 3 h
  4. custombefore being quenched with water (2 mL)
  5. extractionthe organics extracted with EtOAc (3×5 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customPurification by preparative basic HPLC

出典と根拠

ORDレコード
ord-4ffbad2175c947f6baca2627d80488fa
出典データセット
uspto-grants-2013_09
特許番号
US08536214B2

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