Ammonia → HCID 16656818, compound

HRID 578811Notes

Reaction equation

HRID 578811 reaction equation
[C:1]([C:4]1[S:5][CH:6]=[C:7]2[C:12]=1[C:11](=[O:13])[N:10]([C:14]1[CH:19]=[C:18]([S:20]([N:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25][CH2:24]3)(=[O:22])=[O:21])[CH:17]=[CH:16][C:15]=1[Cl:33])[C:9](=[O:34])[NH:8]2)(O)=[O:2].C(N1C=CN=C1)([N:37]1C=CN=C1)=O.N>O1CCCC1.C(OCC)(=O)C>[C:1]([C:4]1[S:5][CH:6]=[C:7]2[C:12]=1[C:11](=[O:13])[N:10]([C:14]1[CH:19]=[C:18]([S:20]([N:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25][CH2:24]3)(=[O:22])=[O:21])[CH:17]=[CH:16][C:15]=1[Cl:33])[C:9](=[O:34])[NH:8]2)(=[O:2])[NH2:37]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 16657781HCID 16657781, compound

Product 1

HCID 16656818HCID 16656818, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-carboxy-3-[2-chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl]thieno[3,4-d]-pyrimidine-2,4(1H,3H)-dione (14 mg) in tetrahydrofuran (1 mL) was added 1,1′-carbonylbis-1H-imidazole (9 mg), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added 28% aqueous ammonia solution (0.5 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: methylene chloride/ methanol=10/1) to give the title compound (13 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. washthe resulting mixture was washed with water and brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: methylene chloride/ methanol=10/1)

Sources & evidence

ORD record
ord-e31eeb498cd14a1fa5b78beec7885cdb
Source dataset
uspto-grants-2015_05
Patent number
US09040693B2

Reaction notes

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