Tetrahydrofuran → HCID 23114738, compound

HRID 2080525Notes

Reaction equation

HRID 2080525 reaction equation
O1CCCC1.C([O:8][C:9](=O)[CH2:10][S:11]([NH:14][C:15]1[CH:20]=[C:19]([CH:21]([S:30]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[F:29])[C:18]([Cl:40])=[CH:17][N:16]=1)(=[O:13])=[O:12])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>CCCCCC.CCOCC>[Cl:40][C:18]1[C:19]([CH:21]([S:30]([C:33]2[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=2)(=[O:32])=[O:31])[C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[F:29])=[CH:20][C:15]([NH:14][S:11]([CH2:10][CH2:9][OH:8])(=[O:13])=[O:12])=[N:16][CH:17]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 58734245HCID 58734245, compound

Product 1

HCID 23114738HCID 23114738, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a tetrahydrofuran (5 ml) solution of ethyl[[[5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amino]sulfonyl]acetate (67 mg, 0.116 mmol) was added an ether solution (0.18 ml) of 1M lithium aluminum hydride at 0° C. The resulting mixture was stirred at 0° C. After the termination of the reaction was confirmed by TLC, a saturated aqueous solution of ammonium chloride was added to the reaction mixture. The resulting mixture was filtered through Celite. The filtrate was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate (=2:1) eluate was concentrated under reduced pressure to give the title compound (39 mg, 0.073 mmol, 63%) as a white solid.

Workup

  1. filtrationThe resulting mixture was filtered through Celite
  2. dry with materialThe filtrate was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. concentrationethyl acetate (=2:1) eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b5f6d5d6551a4ffea34dfe6f30d76ec9
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

Loading…