Water → HCID 117988019, compound

HRID 2206070Notes

Reaction equation

HRID 2206070 reaction equation
[C:1]([C:3]1[C:4]2[C:12]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[N:11][N:10]([C:18]3[CH:19]=[C:20]([C:23]([OH:25])=O)[S:21][CH:22]=3)[C:5]=2[C:6](=[O:9])[NH:7][CH:8]=1)#[N:2].CC[N:28]=C=NCCCN(C)C.O>CC(N(C)C)=O>[C:1]([C:3]1[C:4]2[C:12]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[N:11][N:10]([C:18]3[CH:19]=[C:20]([C:23]([NH2:28])=[O:25])[S:21][CH:22]=3)[C:5]=2[C:6](=[O:9])[NH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 117988608HCID 117988608, compound

Product 1

HCID 117988019HCID 117988019, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 4-(4-cyano-3-cyclopentyl-7-oxo-6,7-dihydro-1H-pyrazolo[3,4-c]pyridin-1-yl)thiophene-2-carboxylic acid (14 mg) obtained in Example 65, EDCI (7.36 mg) and HOBt ammonium salt (18 mg) in DMA (3 mL) was stirred at room temperature for 60 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and crystallized from ethyl acetate/hexane to give the title compound (6.4 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  6. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-88a279998b6e43f2bc6abd171dc892e5
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

Loading…