Ammonia → HCID 18321782, compound

HRID 1871134Notes

Reaction equation

HRID 1871134 reaction equation
[C:1]([C:4]1[N:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([CH2:16][O:17][C:18]3[CH:19]=[CH:20][CH:21]=[C:22]4[C:27]=3[N:26]=[C:25]([CH3:28])[CH:24]=[C:23]4[N:29]3[CH:33]=[CH:32][CH:31]=[N:30]3)[C:10]=2[Cl:34])[CH:6]=[CH:7][CH:8]=1)(O)=[O:2].Cl.C([N:38]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.N>CN(C)C=O.O>[C:1]([C:4]1[N:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([CH2:16][O:17][C:18]3[CH:19]=[CH:20][CH:21]=[C:22]4[C:27]=3[N:26]=[C:25]([CH3:28])[CH:24]=[C:23]4[N:29]3[CH:33]=[CH:32][CH:31]=[N:30]3)[C:10]=2[Cl:34])[CH:6]=[CH:7][CH:8]=1)(=[O:2])[NH2:38]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18321834HCID 18321834, compound

Product 1

HCID 18321782HCID 18321782, compoundYield 38.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-carboxy-1-[2,4-dichloro-3-[2-methyl-4-(pyrazol-1-yl)quinolin-8-yloxymethyl]phenyl]pyrrole (80 mg) in N,N-dimethylformamide (2 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (37.3 mg) and 1-hydroxybenzotriazole (30.7 mg) at ambient temperature; and the mixture was stirred for 1.5 hours at the same temperature. To the mixture was added conc.ammonia solution (12 mg) at ambient temperature, and the mixture was stirred for 2 days at the same temperature. The reaction mixture was poured into water and extracted with chloroform. The separated organic layer was washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (chloroform:methanol=20:1, V/V) to give 2-carbamoyl-1-[2,4-dichloro-3-[2-methyl-4-(pyrazol-1-yl)quinolin-8-yloxymethyl]phenyl]pyrrole (31 mg) as amorphous powder.

Workup

  1. additionTo the mixture was added conc
  2. extractionextracted with chloroform
  3. washThe separated organic layer was washed with water, saturated sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by preparative thin layer chromatography (chloroform:methanol=20:1, V/V)

Sources & evidence

ORD record
ord-ac50efc50dd2434cbad646960effb6fd
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

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