Sodium Carbonate → HCID 178496013, compound

HRID 75529Notes

Reaction equation

HRID 75529 reaction equation
[C:1]([NH:3][C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:5]1[NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH3:21])[CH:19]=2)[N:14]=[C:13]([C:22]([NH:24][CH2:25][CH2:26][O:27][CH3:28])=[O:23])[N:12]=1)#[N:2].Cl.[CH3:30][O:31][NH2:32].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[NH2:2][C:1]([NH:3][C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:5]1[NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH3:21])[CH:19]=2)[N:14]=[C:13]([C:22]([NH:24][CH2:25][CH2:26][O:27][CH3:28])=[O:23])[N:12]=1)=[N:32][O:31][CH3:30]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 866384014-{[(1S,2R)-2-(cyanoamino)cyclohexyl]amino}-N-(2-methoxyethyl)-6-methylquinazolin-2-carboxamide

Product 1

HCID 178496013HCID 178496013, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.96 g of 4-{[(1S,2R)-2-(cyanoamino)cyclohexyl]amino}-N-(2-methoxyethyl)-6-methylquinazolin-2-carboxamide and 8.56 g of methoxyamine hydrochloride in 80 ml of ethanol, 10.86 g of sodium carbonate was added and the mixture was heated at reflux for 1 hour. The reaction solution was added to 400 ml of ice water, and the deposited substance was collected by filtration. After the collected deposited substance was washed with water, it was dried under reduced pressure. The obtained powder was washed with a mixed solution of (chloroform:diisopropyl alcohol=1:1), whereby 1.71 g of a desired compound was obtained as a white powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 hour
  3. filtrationthe deposited substance was collected by filtration
  4. washAfter the collected deposited substance was washed with water, it
  5. customwas dried under reduced pressure
  6. washThe obtained powder was washed with a mixed solution of (chloroform:diisopropyl alcohol=1:1)

Sources & evidence

ORD record
ord-31ac90c69935415cb725f33e43330a81
Source dataset
uspto-grants-2014_09
Patent number
US08835446B2

Reaction notes

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