Hydrochloric Acid → HCID 117667463, compound

HRID 1526220Notes

Reaction equation

HRID 1526220 reaction equation
[Br:1][C:2]1[C:3]([NH:31][C@@H:32]2[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33]2)=[N:4][C:5]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][CH:21]([N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[C:6]([C:8](=[O:10])[NH2:9])[N:7]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>>[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH2:9])=[O:10])[C:5]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][CH:21]([N:24]4[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]4)[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[N:4][C:3]=1[NH:31][C@@H:32]1[CH2:36][CH2:35][NH:34][CH2:33]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 117675697HCID 117675697, compound

Product 1

HCID 117667463HCID 117667463, compoundYield 59%

Procedure

To a mixture of tert-butyl (3R)-3-{[3-bromo-5-carbamoyl-6-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazin-2-yl]amino}pyrrolidine-1-carboxylate (800 mg) was added 4 M hydrochloric acid (12.2 mL), followed by stirring at room temperature for 4 hours. To the reactant was added a 10% aqueous potassium carbonate solution, followed by extraction with a mixed solvent of chloroform:isopropanol (4:1). The organic phase was dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated to obtain 6-bromo-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)-5-[(3R)-pyrrolidin-3-ylamino]pyrazine-2-carboxamide (400 mg) as a yellow solid.

Workup

  1. extractionfollowed by extraction with a mixed solvent of chloroform:isopropanol (4:1)
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2e9afc53dc384086b105a5eb0177f6ac
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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