Trifluoroacetic acid → HCID 66958560, compound

HRID 1364020Notes

Reaction equation

HRID 1364020 reaction equation
FC(F)(F)C(O)=O.[Si:8]([O:15][CH:16]1[CH2:33][N:21]2[C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=[CH:24][C:23]=3[N:32]=[C:20]2[CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]>ClCCl>[Si:8]([O:15][CH:16]1[CH2:33][N:21]2[C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=[CH:24][C:23]=3[N:32]=[C:20]2[CH2:19][NH:18][CH2:17]1)([C:11]([CH3:12])([CH3:13])[CH3:14])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66958543HCID 66958543, compound

Product 1

HCID 66958560HCID 66958560, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (500 mL of a 10% solution in dichloromethane) was added to tert-butyl 11-{[tert-butyl(dimethyl)silyl]oxy}-11,12-dihydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(10H)-carboxylate (9.23 g, 19.7 mmol), and the reaction was stirred at ambient temperature for 75 minutes. The solvent was removed under reduced pressure, and the residue was shaken with triethylamine (300 mL) and dichloromethane. The solution was concentrated under reduced pressure, and the product was dried under high vacuum for two hours to provide 11-{[tert-butyl(dimethyl)silyl]oxy}-9,10,11,12-tetrahydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinoline, which was used in the next step without removing the triethylamine trifluoroacetate salt.

Workup

  1. customThe solvent was removed under reduced pressure
  2. stirringthe residue was shaken with triethylamine (300 mL) and dichloromethane
  3. concentrationThe solution was concentrated under reduced pressure
  4. customthe product was dried under high vacuum for two hours

Sources & evidence

ORD record
ord-9fd1a14c7c264511b6cb3950eda38032
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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