Trifluoroacetic acid → HCID 23653974, compound

HRID 1666641Notes

Reaction equation

HRID 1666641 reaction equation
NN1CCCC1.[C:7]1([CH2:13][C:14]([N:16]2[CH2:20][CH2:19][C@H:18]([NH:21][C:22]3[N:31]=[C:30]([N:32]4[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]4)[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)[CH2:17]2)=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[C:7]1([CH2:13][C:14]([N:16]2[CH2:20][CH2:19][C@H:18]([NH:21][C:22]3[N:31]=[C:30]([N:32]4[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]4)[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)[CH2:17]2)=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 279461-PyrrolidinamineHCID 57970218HCID 57970218, compound

Product 1

HCID 23653974HCID 23653974, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of t-butyl 4-(2-((S)-pyrrolidin-3-ylamino)quinazolin-4-yl)piperazine-1-carboxylate (0.15 g), pyridine (60 mg), and chloroform was added phenylacetic acid chloride (87 mg), and the mixture was stirred at room temperature for 16 h. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate, the mixture was extracted with chloroform, and the organic layer was dried with anhydrous magnesium sulfate. The desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=2:1−ethyl acetate) to obtain t-butyl 4-(2-((S)-1-(2-phenylethanoyl)pyrrolidin-3-ylamino)quinazolin-4-yl)piperazine-1-carboxylate (0.12 g). (2) To t-butyl 4-(2-((S)-1-(2-phenylethanoyl)pyrrolidin-3-ylamino)quinazolin-4-yl)piperazine-1-carboxylate (0.12 g) was added a mixed solution (7.5 mL) of chloroform and trifluoroacetic acid (10:1), and the mixture was stirred overnight at room temperature. To the reaction mixture was added 1 M aqueous sodium hydroxide, the mixture was extracted with chloroform, and the organic layer was dried with anhydrous magnesium sulfate. The desiccant was removed by filtration, then the solvent was evaporated, and the residue was purified by preparative TLC to obtain title compound (69 mg).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  3. customThe desiccant was removed by filtration
  4. customthe solvent was evaporated
  5. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-87d1e0332f364547a2871ca914bed6c9
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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