Triethylamine → HCID 9907487, compound

HRID 863510Notes

Reaction equation

HRID 863510 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C.[NH2:28][CH:29]1[CH2:46][C:32]2[C:33]3[NH:34][C:35](=[O:45])[C:36](=[O:44])[NH:37][C:38]=3[CH:39]=[C:40]([N+:41]([O-:43])=[O:42])[C:31]=2[CH2:30]1>O1CCCC1.CN(C)C=O>[N+:41]([C:40]1[C:31]2[CH2:30][CH:29]([NH:28][C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[O:8])[CH2:46][C:32]=2[C:33]2[NH:34][C:35](=[O:45])[C:36](=[O:44])[NH:37][C:38]=2[CH:39]=1)([O-:43])=[O:42]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 107002-Thiophenecarboxylic acidHCID 682631,1'-CarbonyldiimidazoleHCID 19696216HCID 19696216, compound

Product 1

HCID 9907487HCID 9907487, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of thiophene-2-carboxylic acid (1 mmol) in anhydrous tetrahydrofuran (THF) was treated with carbonyldiimidazole (1.2 mmol) and triethyl amine (1 mL) and heated at 60° C. for 30 min. After cooling to room temperature a solution of 8-amino-6-nitro-4,7,8,9,-tetrahydro-1H-cyclopenta[f]quinoxaline-2,3-dione (1 mmol) in dimethylformamide (DMF) was added. The reaction mixture as stirred at room temperature for 2 h, then heated at 70° C. for 2 h. The solvent was evaporated and the residue triturated with acetone. The solid was collected by filtration, washed with diethyl ether and dried in vacuo. Calc'd for C16H12N4O5S.H2O: C, 49.22; H, 3.61; N, 14.35, found: C, 49.06; H, 312; N, 15.05. MS M+1 (373).

Workup

  1. additionwas added
  2. temperatureheated at 70° C. for 2 h
  3. customThe solvent was evaporated
  4. customthe residue triturated with acetone
  5. filtrationThe solid was collected by filtration
  6. washwashed with diethyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-3f3813be66cc4757865aab6455d457c9
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

Loading…