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Sodium Thiosulfate → 2-methyl-propane-1-sulfonic acid [2,4-difluoro-3-(4-methyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-amide

HRID 1187308
ノート
印刷プレビュー

反応式

HRID 1187308 の反応式
[F:1][C:2]1[C:7]([CH:8]([OH:19])[C:9]2[C:17]3[C:16]([CH3:18])=[N:15][CH:14]=[N:13][C:12]=3[NH:11][CH:10]=2)=[C:6]([F:20])[CH:5]=[CH:4][C:3]=1[NH:21][S:22]([CH2:25][CH:26]([CH3:28])[CH3:27])(=[O:24])=[O:23].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[F:1][C:2]1[C:7]([C:8]([C:9]2[C:17]3[C:16]([CH3:18])=[N:15][CH:14]=[N:13][C:12]=3[NH:11][CH:10]=2)=[O:19])=[C:6]([F:20])[CH:5]=[CH:4][C:3]=1[NH:21][S:22]([CH2:25][CH:26]([CH3:28])[CH3:27])(=[O:24])=[O:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 583169882-methyl-propane-1-sulfonic acid {2,4-difluoro-3-[hydroxy-(4-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-amide

生成物 1

HCID 532386672-methyl-propane-1-sulfonic acid [2,4-difluoro-3-(4-methyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-amide
収率 28.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 2-methyl-propane-1-sulfonic acid {2,4-difluoro-3-[hydroxy-(4-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-amide (77, 99 mg, 0.24 mmol) in 2 mL of tetrahydrofuran, Dess-Martin periodinane (112 mg, 0.265 mmol) is added and the reaction is stirred at room temperature for 2 hours. The reaction is poured into saturated aqueous sodium thiosulfate along with some sodium bicarbonate solid and extracted with ethyl acetate. The organic layer is washed with water, then brine, and dried with sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with ethyl acetate and dichloromethane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (P-1003, 28 mg). MS (ESI) [M+H+]+=409.3.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with water
  3. dry with materialbrine, and dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe resulting material is purified by silica gel column chromatography
  7. washeluting with ethyl acetate and dichloromethane
  8. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-970ca070fc4c4ee0a9d859073149811f
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08673928B2

反応ノート

読み込み中…

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