Hydrochloric Acid → HCID 178470387, compound
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:12])=[CH:9][C:10]=1[NH2:11])=[O:5])[CH3:2].[ClH:13].O1CCOCC1.[C:20](#[N:22])[CH3:21]>>[ClH:13].[C:20]([NH:11][C:10]1[CH:9]=[C:8]([CH3:12])[NH:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5])(=[NH:22])[CH3:21]Participants
Conditions
- Temperature
- 50 °C
Procedure
Ethyl-3-amino-5-methyl-1H-pyrrole-2-carboxylate (58.87 g; 0.35 mol) prepared according to literature [Gangjee A.; Li W.; Yang J.; Kisliuk R. L.; J. Med. Chem. 2008, 51, 68] is suspended in acetonitrile (1750 mL). To the suspension is added dropwise 4M HCl in dioxane (473 mL; 1.89 mol) within 15 minutes. After complete addition the reaction mixture is heated to 50° C. for 18 hours. The reaction mixture is cooled to 10° C., the solid is collected by suction filtration and washed with cold acetonitrile (400 mL). A second crop of product is obtained from the mother liquor after concentration under reduced pressure. The residue is collected with t-butylmethyl-ether. After the suction filtration the solids are combined and dried in vacuum at 50° C. to yield the title compound as off-white solid.
Workup
- additionAfter complete addition the reaction mixture
- temperatureThe reaction mixture is cooled to 10° C.
- filtrationthe solid is collected by suction filtration
- washwashed with cold acetonitrile (400 mL)
- customA second crop of product is obtained from the mother liquor
- concentrationafter concentration under reduced pressure
- customThe residue is collected with t-butylmethyl-ether
- filtrationAfter the suction filtration the solids
- customdried in vacuum at 50° C.
Sources & evidence
- ORD record
- ord-56ebc60dd5f7432cb3466689ba1ff43a
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376442B2
Reaction notes
Loading…