Ammonium Chloride → HCID 86723887, compound

HRID 576780Notes

Reaction equation

HRID 576780 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[C:15](=[O:33])[N:16]([CH3:32])[C:17](=[O:31])[N:18]([C:21]4[CH:22]=[C:23](CC(O)=O)[CH:24]=[CH:25][CH:26]=4)[C:19]=3[CH3:20])=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2].[OH:34]N1C2N=CC=CC=2N=N1.C([N:46]([CH:49](C)C)CC)C.[Cl-].[NH4+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]([C:14]3[C:15](=[O:33])[N:16]([CH3:32])[C:17](=[O:31])[N:18]([C:21]4[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=4)[C:49]([NH2:46])=[O:34])[C:19]=3[CH3:20])=[CH:12][CH:11]=[N:10]2)=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 181649HOAtHCID 521913N,N-Diethyl-2-propanamineHCID 86723888HCID 86723888, compound

Product 1

HCID 86723887HCID 86723887, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-[5-[1-(4-cyanophenyl)1H-pyrazol-5-yl]-3,6-dimethyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)yl]phenylacetic acid (prepared in Example 103), benzotriazol-1-yl-oxytripyrrolidine phosphonium hexafluorophosphate (30.8 mg), 1-hydroxy-7-azabenzotriazole (8.6 mg) and N,N-diethylisopropylamine (76 μl) in N,N-dimethy formamide (0.7 ml) was stirred at room temperature for thirty minutes. Thereto was added ammonium chloride (15.7 mg) and the resulting mixture was stirred at room temperature for twenty-two hours, and to the reaction mixture was added ethyl acetate (30 ml) and the resulting mixture was washed with 1M hydrochloric acid (10 ml) and saturated saline (10 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol) to afford 3-(5-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-3,6-dimethyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)benzamide (18.0 mg).

Workup

  1. washthe resulting mixture was washed with 1M hydrochloric acid (10 ml) and saturated saline (10 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-9fafa80fdf4748ccb05b16346e487a96
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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