Ammonia → HCID 86627526, compound

HRID 1970017Notes

Reaction equation

HRID 1970017 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.COS(OC)(=O)=O.[O:15]=[C:16]1[C:25]2[NH:26][CH:27]=[CH:28][C:24]=2[C:23]2[CH:22]=[C:21]([S:29](=[O:38])(=[O:37])[NH:30][CH:31]3CCNCC3)[CH:20]=[CH:19][C:18]=2[NH:17]1.[CH:39]1([C:44]([O-:46])=[O:45])[CH2:43][CH2:42][CH2:41][CH2:40]1.N>CN(C)C=O.O>[CH3:1][N:3]1[CH2:6][CH2:7][CH:31]([NH:30][S:29]([C:21]2[CH:20]=[CH:19][C:18]3[NH:17][C:16](=[O:15])[C:25]4[NH:26][CH:27]=[CH:28][C:24]=4[C:23]=3[CH:22]=2)(=[O:37])=[O:38])[CH2:5][CH2:4]1.[CH:39]1([C:44]([O-:46])=[O:45])[CH2:43][CH2:42][CH2:41][CH2:40]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 86627527HCID 86627527, compound

Product 1

HCID 86627526HCID 86627526, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

83 μL (0.6 mmol) of triethylamine and 22 μL (0.24 mmol) of dimethylsulfate are added to a solution of 55 mg (0.12 mmol) of 4-oxo-8-(piperidin-4-ylsulfamoyl)-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-cyclopentyl carboxylate dissolved in 5 mL of anhydrous dimethylformamide. The solution is stirred at room temperature for 3 hours before adding 2 mL of ammonia. After stirring for a further 10 minutes, water is added and the product is extracted with ethyl acetate. The organic phases are dried over magnesium sulfate, filtered and evaporated. The residue is purified by chromatography on silica (eluent chloroform/methanol/ammonia 300/24/4) to give 22 mg (39%) of 8-(1-methyl-piperidin-4-ylsulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-cyclopentyl carboxylate in the form of a white solid.

Workup

  1. stirringAfter stirring for a further 10 minutes
  2. extractionthe product is extracted with ethyl acetate
  3. dry with materialThe organic phases are dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by chromatography on silica (eluent chloroform/methanol/ammonia 300/24/4)

Sources & evidence

ORD record
ord-7433407c68b24b508b9839b681525101
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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