Sodium sulfate decahydrate → HCID 57502448, compound

HRID 1926655Notes

Reaction equation

HRID 1926655 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[N:25]=[C:24]([O:26][CH:27]5[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]5)[CH:23]=[N:22][CH:21]=4)=[CH:18][N:17]([S:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)(=[O:42])=[O:41])[C:14]3=[N:15][CH:16]=2)[CH:8]=[N:7]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[OH:3][CH2:4][CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[N:25]=[C:24]([O:26][CH:27]5[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34])[CH2:31][CH2:32]5)[CH:23]=[N:22][CH:21]=4)=[CH:18][N:17]([S:40]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)(=[O:41])=[O:42])[C:14]3=[N:15][CH:16]=2)[CH:8]=[N:7]1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 57502447HCID 57502447, compound

Product 1

HCID 57502448HCID 57502448, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 4-({6-[5-[1-(2-ethoxy-2-oxoethyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrazin-2-yl}oxy)piperidine-1-carboxylate (0.10 g, 0.15 mmol) in tetrahydrofuran (2 mL) was added lithium aluminium hydride (11 mg, 0.29 mmol) (CAUTION: GAS EVOLUTION). The reaction mixture was stirred at room temperature for 2.5 h then cooled in an ice bath. Sodium sulfate decahydrate (0.32 mL, 1.5 mmol) was added to the reaction mixture slowly (CAUTION: GAS EVOLUTION). The reaction mixture was warmed to room temperature and filtered through celite. The filtrate was concentrated to a crude solid and purified by reverse phase HPLC to afford tert-butyl 4-({6-[5-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrazin-2-yl}oxy)piperidine-1-carboxylate. LRMS (ESI) calculated for C32H35N7O6S [M+H]+, 646.2; found 646.2.

Workup

  1. temperaturethen cooled in an ice bath
  2. temperatureThe reaction mixture was warmed to room temperature
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated to a crude solid
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-d5970f45ecd7488e96c386413e38a0a0
Source dataset
uspto-grants-2012_05
Patent number
US08183245B2

Reaction notes

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