HCID 57454228, compound → Onvansertib

HRID 1914762Notes

Reaction equation

HRID 1914762 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:16]2[C:15]3[N:14]=[C:13]([NH:17][C:18]4[CH:23]=[C:22]([N:24]5[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]5)[CH:21]=[CH:20][C:19]=4[O:31][C:32]([F:35])([F:34])[F:33])[N:12]=[CH:11][C:10]=3[CH2:9][CH2:8][C:7]=2[C:6]([C:36]([O-:38])=O)=[N:5]1.[K+].[N:40]1(C([O-])=O)C2C=CC=CC=2N=N1.[NH4+]>CC(N(C)C)=O.O>[OH:1][CH2:2][CH2:3][N:4]1[C:16]2[C:15]3[N:14]=[C:13]([NH:17][C:18]4[CH:23]=[C:22]([N:24]5[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]5)[CH:21]=[CH:20][C:19]=4[O:31][C:32]([F:33])([F:35])[F:34])[N:12]=[CH:11][C:10]=3[CH2:9][CH2:8][C:7]=2[C:6]([C:36]([NH2:40])=[O:38])=[N:5]1

Participants

5

Reactant 2

HCID 57454228HCID 57454228, compoundHCID 68668260HCID 68668260, compound

Product 1

HCID 49792852OnvansertibYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

A suspension of potassium 1-(2-hydroxy-ethyl)-8-[5-(4-methyl-piperazin-1-yl)-2-trifluoromethoxy-phenylamino]-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate (1.54 g, 2.69 mmol) in anhydrous DMA (40 mL) was treated with N-ethyl-N′,N′-diisopropyl carbodiimide hydrochloride (EDCI) (1.03 g, 5.38 mmol) and with ammonium 1H-1,2,3-benzotriazol-1-ate (0.819 g, 5.38 mmol). The reaction was stirred at room temperature overnight. The reaction was diluted with water and the resulting precipitate was collected by filtration to afford the title compound (1.32 g, 88% yield).

Workup

  1. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-ebc518a07d3f4a959864e53a2c8f9f71
Source dataset
uspto-grants-2013_12
Patent number
US08614220B2

Reaction notes

Loading…