Triethylamine → 1-Methyl-3-(1-methyl-4-piperindin-4-yl)-5-hydroxy-1H-indole2,6-difluorobenzenesulfonicacidesteroxalate

HRID 1766268ノート

反応式

HRID 1766268 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[S:9](Cl)(=[O:11])=[O:10].[CH3:13][N:14]1[C:22]2[C:17](=[CH:18][C:19]([OH:23])=[CH:20][CH:21]=2)[C:16]([CH:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[CH:15]1.C(N(CC)CC)C.[C:38]([O-:41])([OH:40])=O.[Na+]>C(Cl)Cl.O1CCCC1.CN(C=O)C.O.C(OCC)(=O)C>[C:19]([OH:23])(=[O:10])[C:38]([OH:41])=[O:40].[CH3:13][N:14]1[C:22]2[C:17](=[CH:18][C:19]([O:23][S:9]([C:3]3[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])(=[O:11])=[O:10])=[CH:20][CH:21]=2)[C:16]([CH:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[CH:15]1

参加物

10

反応物 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27342712,6-Difluorobenzenesulfonyl chlorideHCID 179801241-methyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-ol

生成物 1

HCID 248800401-Methyl-3-(1-methyl-4-piperindin-4-yl)-5-hydroxy-1H-indole2,6-difluorobenzenesulfonicacidesteroxalate

試薬・触媒・溶媒 5

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 2,6-difluorobenzenesulfonyl chloride (312 mg, 1.47 mmol) in methylene chloride (2 mL) was added to a solution of 1-methyl-3-(1-methylpiperidin-4-yl)-5-hydroxy-1H-indole (327 mg, 1.34 mmol) and triethylamine (226 μL, 1.6 mmol) in tetrahydrofuran (10 mL), methylene chloride (2 mL) and DMF (6 mL). The reaction mixture was stirred at ambient temperature for 1 h. The reaction mixture was diluted with water and ethyl acetate, basified with saturated NaHCO3, and extracted with ethyl acetate. The ethyl acetate extracts were washed with water, brine, dried (NaSO4), filtered and concentrated under reduced pressure to give 550 mg of a white solid. The product was purified by flash chromatography (silica gel, 5%,10% 2M ammonia in methanol/methylene chloride) to give 440 mg (78%) of homogeneous title compound as a white foam. The product was crystallized as the oxalic acid salt from ethyl acetate to give a white powder: mp=195-198° C. dec; MS(m/e): 421 (M+1); Calculated for C23H22F2N2O3S.C2H2O4: C, 54.11; H, 4.74; N, 5.49. Found: C, 53.86; H, 4.62; N, 5.29.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate extracts were washed with water, brine
  3. dry with materialdried (NaSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-138d9481a45d42c696d5bfc47b391bf5
出典データセット
uspto-grants-2007_06
特許番号
US07230011B2

反応ノート

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