Sodium Carbonate → HCID 67166898, compound

HRID 2088863Notes

Reaction equation

HRID 2088863 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:13][C:14]1[N:23]([CH2:24][CH3:25])[C:22]2[N:21]=[C:20]([C:26]3[CH:31]=[CH:30][C:29]([CH2:32][C:33](O)=[O:34])=[CH:28][CH:27]=3)[CH:19]=[CH:18][C:17]=2[C:16](=[O:36])[C:15]=1[C:37](=[O:40])[NH:38][CH3:39].[ClH:41].[CH3:42][CH:43]([N:45]1[CH2:50][CH2:49][O:48][CH2:47][CH:46]1[CH2:51][NH2:52])[CH3:44].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[ClH:41].[NH2:13][C:14]1[N:23]([CH2:24][CH3:25])[C:22]2[C:17]([C:16](=[O:36])[C:15]=1[C:37]([NH:38][CH3:39])=[O:40])=[CH:18][CH:19]=[C:20]([C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([NH:52][CH2:51][CH:46]3[CH2:47][O:48][CH2:49][CH2:50][N:45]3[CH:43]([CH3:44])[CH3:42])=[O:34])=[CH:28][CH:27]=1)[N:21]=2

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 67166426HCID 67166426, compoundHCID 67167837HCID 67167837, compound

Product 1

HCID 67166898HCID 67166898, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under an inert atmosphere, 0.18 g of N,N-carbonyldiimidazole is added to a suspension of 0.4 g (1.1 mmol) of the compound obtained from step 2.5 in DMF (5 ml). The reaction mixture is stirred at room temperature for 1 hour 30 minutes, 0.225 g (1.2 mmol) of the compound obtained from step 2.2 dissolved in DMF (1 ml), and stirred beforehand in the presence of 0.13 g (1.3 mmol) of sodium carbonate, is then added and the mixture is heated at 80° C. for 2 hours. The DMF is removed by evaporation under reduced pressure, and the residue is then purified by flash chromatography on silica gel (eluent: dichloromethane/methanol/1% NH4OH), with a gradient of 0% to 5% methanol. 0.3 g of product is obtained, in the form of a white powder. Yield: 57%. MH+: 521.3

Workup

  1. additionis then added
  2. temperaturethe mixture is heated at 80° C. for 2 hours
  3. customThe DMF is removed by evaporation under reduced pressure
  4. customthe residue is then purified by flash chromatography on silica gel (eluent: dichloromethane/methanol/1% NH4OH), with a gradient of 0% to 5% methanol

Sources & evidence

ORD record
ord-edc7728f9aab473daa401fbf80b63c41
Source dataset
uspto-grants-2013_05
Patent number
US08436011B2

Reaction notes

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