Hydrochloric Acid → HCID 117667209, compound

HRID 1526214Notes

Reaction equation

[C:1]([C:4]1[N:5]=[C:6]([Cl:41])[C:7]([NH:28][C@@H:29]2[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30]2)=[N:8][C:9]=1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:26][CH2:25][C:20]3(OCC[O:21]3)[CH2:19][CH2:18]2)=[C:13]([CH3:27])[CH:12]=1)(=[O:3])[NH2:2].Cl.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[K+].[K+]>>[Cl:41][C:6]1[N:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:26][CH2:25][C:20](=[O:21])[CH2:19][CH2:18]3)=[C:13]([CH3:27])[CH:12]=2)=[N:8][C:7]=1[NH:28][C@@H:29]1[CH2:33][CH2:32][NH:31][CH2:30]1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 11430Potassium Carbonate

HCID 516892Sodium Bicarbonate

HCID 117675635HCID 117675635, compound

Product 1

HCID 117667209HCID 117667209, compoundYield 77.1%

Conditions

Temperature: 80 °C

Procedure

A mixture of tert-butyl (3R)-3-[(5-carbamoyl-3-chloro-6-{[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-3-methylphenyl]amino}pyrazin-2-yl)amino]pyrrolidine-1-carboxylate (850 mg) and 3 M hydrochloric acid (9.6 mL) was stirred at 80° C. for 3 hours. The reactant was left to be cooled, and then a saturated aqueous sodium hydrogen carbonate solution and a 10% aqueous potassium carbonate solution were added thereto, followed by stirring at room temperature for 30 minutes. The precipitated solid was collected by filtration, washed with water, and then dried under reduced pressure to obtain 6-chloro-3-{[3-methyl-4-(4-oxopiperidin-1-yl)phenyl]amino}-5-[(3R)-pyrrolidin-3-ylamino]pyrazine-2-carboxamide (495 mg) as a pale yellow solid.

Workup

waitThe reactant was left
temperatureto be cooled
stirringby stirring at room temperature for 30 minutes
filtrationThe precipitated solid was collected by filtration
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-96702a0837eb4a1bb1f54d53e5936c1c
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085540B2

Reaction notes

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