Hydrochloric Acid → HCID 67442213, compound

HRID 1666605Notes

Reaction equation

HRID 1666605 reaction equation
NN1CCCC1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([N:17]2[CH2:21][CH2:20][C@H:19]([NH:22][C:23]3[N:32]=[C:31]([N:33]4[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]4)[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)[CH2:18]2)=[O:16])=[CH:10][CH:9]=1.[ClH:46]>CO.C(OCC)(=O)C>[ClH:7].[ClH:46].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][C:15]([N:17]2[CH2:21][CH2:20][C@H:19]([NH:22][C:23]3[N:32]=[C:31]([N:33]4[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]4)[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)[CH2:18]2)=[O:16])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 279461-PyrrolidinamineHCID 57970094HCID 57970094, compound

Product 1

HCID 67442213HCID 67442213, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of t-butyl 4-(2-((S)-pyrrolidin-3-ylamino)quinazolin-4-yl)piperazine-1-carboxylate (0.30 g), p-chlorophenylacetic acid (0.13 g), and chloroform (5 mL) were added HOBt.H2O (0.18 g) and EDC.HCl (0.18 g), and the mixture was stirred at room temperature for 2 days. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with chloroform. The organic layer was dried with anhydrous sodium sulfate, the desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=3:2) to obtain t-butyl 4-(2-((S)-1-(2-(4-chlorophenyl)ethanoyl)pyrrolidin-3-ylamino)quinazolin-4-yl)piperazine-1-carboxylate (0.29 g). (2) To a solution of t-butyl 4-(2-((S)-1-(2-(4-chlorophenyl)ethanoyl)pyrrolidin-3-ylamino)quinazolin-4-yl)piperazine-1-carboxylate (0.28 g) in methanol (5 mL) was added a solution (1.3 mL) of 4 M HCl in ethyl acetate, and the mixture was stirred overnight. The solvent was evaporated under reduced pressure, and the residue was crystallized in diethyl ether to obtain the title compound (0.15 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was crystallized in diethyl ether

Sources & evidence

ORD record
ord-b284ae83416c482980bf0ad33bf6839c
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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