Tetrahydrofuran → HCID 67346331, compound

HRID 1257737Notes

Reaction equation

HRID 1257737 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][CH2:22][CH2:21][CH:20]([NH:24][C:25]4[C:30]([N+:31]([O-])=O)=[CH:29][N:28]=[C:27]5[N:34]([S:37]([C:40]6[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=6)(=[O:39])=[O:38])[CH:35]=[CH:36][C:26]=45)[CH2:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C1COCC1>[Pd].CCO>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][CH2:22][CH2:21][CH:20]([NH:24][C:25]4[C:30]([NH2:31])=[CH:29][N:28]=[C:27]5[N:34]([S:37]([C:40]6[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=6)(=[O:39])=[O:38])[CH:35]=[CH:36][C:26]=45)[CH2:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 67344923HCID 67344923, compound

Product 1

HCID 67346331HCID 67346331, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 3-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (7.09 g, 11.4 mmol) and palladium on carbon (2.1 g, 10%, wet, Degussa, E101 NE/W) in a 4:1 mixture of THF and EtOH (100 ml) was stirred under a hydrogen atmosphere (2 balloons) at 50° C. for 6 h. The reaction mixture was cooled to 25° C. and was filtered through Celite. The Celite was washed with THF (2×25 ml), and the combined filtrate and washings were concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (gradient: 0 to 7% CH3OH in CH2Cl2) gave 3-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (5.76 g, 85%, purple foam) still containing some impurities. This material was used in the next step below without additional purification or characterization.

Workup

  1. temperatureThe reaction mixture was cooled to 25° C.
  2. filtrationwas filtered through Celite
  3. washThe Celite was washed with THF (2×25 ml)
  4. concentrationthe combined filtrate and washings were concentrated under reduced pressure
  5. customPurification of the residue by column chromatography on silica gel (gradient: 0 to 7% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-b3c0329de11c46ae850a18b4aa4a50d2
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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