Hydrochloric Acid → 4-{1-[1-(ethylsulfonyl)-3-(fluoromethyl)azetidin-3-yl]-1H-pyrazol-4-yl}-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine

HRID 1692986ノート

反応式

HRID 1692986 の反応式
[F:1][CH2:2][C:3]1([N:14]2[CH:18]=[C:17]([C:19]3[C:20]4[CH:27]=[CH:26][N:25]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:21]=4[N:22]=[CH:23][N:24]=3)[CH:16]=[N:15]2)[CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1.Cl.O1CCOCC1.C(#N)C.C(N(CC)CC)C.[CH2:53]([S:55](Cl)(=[O:57])=[O:56])[CH3:54]>>[CH2:53]([S:55]([N:5]1[CH2:6][C:3]([N:14]2[CH:18]=[C:17]([C:19]3[C:20]4[CH:27]=[CH:26][N:25]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:34])([CH3:33])[CH3:35])[C:21]=4[N:22]=[CH:23][N:24]=3)[CH:16]=[N:15]2)([CH2:2][F:1])[CH2:4]1)(=[O:57])=[O:56])[CH3:54]

参加物

7

反応物 6

HCID 313Hydrochloric Acid2 回HCID 6342AcetonitrileHCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 312751,4-DioxaneHCID 66824231tert-butyl 3-(fluoromethyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylate

生成物 1

HCID 668242874-{1-[1-(ethylsulfonyl)-3-(fluoromethyl)azetidin-3-yl]-1H-pyrazol-4-yl}-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine

実験手順

tert-Butyl 3-(fluoromethyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylate (0.120 g, 0.239 mmol) was treated with 4.00 M of hydrogen chloride in 1,4-dioxane (1.0 mL, 4.0 mmol) at rt for 1 h, then evaporated to dryness under reduced pressured. LCMS (M+H) 403.4. To the resultant crude HCl salt in acetonitrile (4 mL, 80 mmol) was added triethylamine (0.0998 ML, 0.716 mmol) followed by ethanesulfonyl chloride (0.0317 mL, 0.334 mmol). The mixture was stirred at rt for 30 min. After quenching with aq. sodium bicarbonate, the mixture was extracted with dichloromethane. The combined organic layers were washed with water, brine and dried over sodium sulfate, evaporated to dry. The residue was used directly in next step. LCMS calculated for C21H32FN6O3SSi(M+H)+: m/z=495.2; Found: 495.4.

後処理

  1. customevaporated to dryness under reduced pressured
  2. customAfter quenching with aq. sodium bicarbonate
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customto dry

出典と根拠

ORDレコード
ord-47c600e732524a09962a4749a69b2c19
出典データセット
uspto-grants-2012_04
特許番号
US08158616B2

反応ノート

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