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Pyridine → HCID 57970218, compound

HRID 1666640
Notes
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Reaction equation

HRID 1666640 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7]2[N:16]=[C:15]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH2:2]1.N1C=CC=CC=1.[C:36]1([CH2:42][C:43](Cl)=[O:44])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:36]1([CH2:42][C:43]([N:1]2[CH2:5][CH2:4][C@H:3]([NH:6][C:7]3[N:16]=[C:15]([N:17]4[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]4)[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[N:8]=3)[CH2:2]2)=[O:44])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1049PyridineHCID 7679Phenylacetyl chlorideHCID 516892Sodium BicarbonateHCID 57970081HCID 57970081, compound

Product 1

HCID 57970218HCID 57970218, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 6212
Chloroform
Solvent

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. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=2:1−ethyl acetate)

Sources & evidence

ORD record
ord-325084d341ab427c8a59ebc30d1f6666
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08044068B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes