Ammonia → HCID 135848090, compound

HRID 498050Notes

Reaction equation

HRID 498050 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]2[N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[N:13]=[C:14]([CH2:15][C:16](O)=[O:17])[C:3]1=2.O1CCCC1.C(N1C=CN=C1)([N:32]1C=CN=C1)=O.N>O.CN(C)C=O>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]2[N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[N:13]=[C:14]([CH2:15][C:16]([NH2:32])=[O:17])[C:3]1=2

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 135848084HCID 135848084, compound

Product 1

HCID 135848090HCID 135848090, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[4-oxo-1-(2-pyridinyl)-4,9-dihydro-1H-pyrazolo[3,4-b]quinolin-3-yl]acetic acid (1.60 g, 5.0 mmol) in a mixed solvent of tetrahydrofuran (100 mL) and N,N-dimethylformamide (20 mL), 1,1′-carbonyldiimidazole (0.89 g, 5.5 mmol) was added and the mixture was stirred at room temperature for 30 minutes. Subsequently, 25% aqueous ammonia solution was added to the mixture and the resulting solution was stirred at room temperature for 1 hour. The solution was poured into water, and the resulting precipitate was collected by filtration. The collected crude crystals were washed with water, and dried to give the title compound (0.94 g, 59% yield).

Workup

  1. stirringthe resulting solution was stirred at room temperature for 1 hour
  2. filtrationthe resulting precipitate was collected by filtration
  3. customThe collected crude crystals
  4. washwere washed with water
  5. customdried

Sources & evidence

ORD record
ord-a338ab089d8f4a13b1c782fa86507840
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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