Trifluoroacetic acid → HCID 67426700, compound

HRID 888973Notes

Reaction equation

HRID 888973 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:16]([CH:33]2[CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34]2)[C:17]2[C:22]([N:23]=1)=[C:21]([N:24]1[CH2:29][CH2:28][N:27]([CH2:30][CH3:31])[CH2:26][CH2:25]1)[N:20]=[C:19]([CH3:32])[N:18]=2>ClCCl>[NH:35]1[CH2:34][CH:33]([N:16]2[C:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[Cl:8])=[N:23][C:22]3[C:17]2=[N:18][C:19]([CH3:32])=[N:20][C:21]=3[N:24]2[CH2:25][CH2:26][N:27]([CH2:30][CH3:31])[CH2:28][CH2:29]2)[CH2:36]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67425498HCID 67425498, compound

Product 1

HCID 67426700HCID 67426700, compoundYield 116.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (15 mL) to a solution of tert-butyl 3-(8-(2-chlorophenyl)-6-(4-ethylpiperazin-1-yl)-2-methyl-9H-purin-9-yl)azetidine-1-carboxylate (0.005 mol, 3.0 g) in dichloromethane (15 mL) at 0° C. and stir for 2 hours at room temperature. Quench the reaction mixture with saturated sodium bicarbonate solution and extract with dichloromethane. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to give 9-(azetidin-3-yl)-8-(2-chlorophenyl)-6-(4-ethylpiperazin-1-yl)-2-methyl-9H-purine (2.4 g). MS (m/z): 412.22 (M+1).

Workup

  1. customQuench the reaction mixture with saturated sodium bicarbonate solution
  2. extractionextract with dichloromethane
  3. dry with materialDry the organic layer over anhydrous sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-fe21ffafdde74ae583bcc45819707dad
Source dataset
uspto-grants-2012_08
Patent number
US08252798B2

Reaction notes

Loading…