Trifluoroacetic acid → HCID 58574834, compound

HRID 1619297Notes

Reaction equation

HRID 1619297 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:33])[N:15]([CH2:20][CH:21]4[CH2:25][CH2:24][CH2:23][N:22]4C(OC(C)(C)C)=O)[CH:16]=[N:17]3)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:33])[N:15]([CH2:20][CH:21]4[CH2:25][CH2:24][CH2:23][NH:22]4)[CH:16]=[N:17]3)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 58574392HCID 58574392, compound

Product 1

HCID 58574834HCID 58574834, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 2-((7-((3-fluorophenyl)ethynyl)-4-oxoquinazolin-3(4H)-yl)methyl)pyrrolidine-1-carboxylate (0.74 g) and TFA (4 mL) in dichloromethane (4 mL) was stirred at room temperature for 2.5 h. Then the reaction mixture was adjusted pH to 8-9 with saturated NaHCO3 and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over Na2SO4 and concentrated to give the crude product (0.4 g), which was used for the next step without further purification. MS (ESI): 348 (MH+).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6ea841cbd7164983b176d00412ef73da
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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