Ethanol → HCID 73442248, compound

HRID 1049844Notes

Reaction equation

HRID 1049844 reaction equation
[OH:1][CH2:2][C:3]#[C:4][C:5]1[NH:24][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:13][C:14]3[CH:23]=[CH:22][C:17]4[NH:18][C:19](=[O:21])[S:20][C:16]=4[CH:15]=3)[C:7]=2[CH:6]=1.C(O)C>[Pd].O1CCCC1>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[NH:24][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:13][C:14]3[CH:23]=[CH:22][C:17]4[NH:18][C:19](=[O:21])[S:20][C:16]=4[CH:15]=3)[C:7]=2[CH:6]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 73442190HCID 73442190, compound

Product 1

HCID 73442248HCID 73442248, compoundYield 4.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture comprising 262 mg (777 μmol) 6-{[6-(3-hydroxyprop-1-yn-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}-1,3-benzothiazol-2(3H)-one (prepared according to example 11), 15 mL ethanol, 5 mL tetrahydrofuran and 41.3 mg palladium on charcoal (10%) were stirred at 23° C. under an atmosphere of hydrogen overnight. After filtration and removal of the solvents the crude product was purified by chromatography and crystallization to give 12 mg (4%) of the title compound.

Workup

  1. filtrationAfter filtration and removal of the solvents the crude product
  2. customwas purified by chromatography and crystallization

Sources & evidence

ORD record
ord-899f7bfb474f48edb45aae1dd17d417c
Source dataset
uspto-grants-2016_07
Patent number
US09382255B2

Reaction notes

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