Trifluoroacetic acid → HCID 70207845, compound

HRID 611563Notes

Reaction equation

HRID 611563 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[O:21][C:20]2[C:15](=[N:16][CH:17]=[C:18]([Cl:22])[CH:19]=2)[CH:14]=1)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[ClH:22].[ClH:22].[Cl:22][C:18]1[CH:19]=[C:20]2[O:21][C:13]([C@@H:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)=[CH:14][C:15]2=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 18396231HCID 18396231, compound

Product 1

HCID 70207845HCID 70207845, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 2 g sample of the compound from step 7b above in 10 mL of CH2Cl2 at 0° C. was added 10 mL of TFA, and the reaction mixture was stirred for 1 hour, poured into saturated aqueous Na2CO3 and extracted with CH2Cl2. The organic extract was dried over MgSO4, and the solvent was removed. The residue was chromatographed on silica gel, eluting with 99:1 to 95:5 CHCl3 :MeOH. The product was treated with HCl/ether, and the salt was recrystallized from EtOH/EtOAc to give 1.2 g of title compound: 1H NMR (D2O, 300 MHz) δ 2.18-2.50 (m, 3H), 2.54-2.65 (m, 1H), 3.51-3.36 (m, 2H), 5.06 (t, 1H, J=8 Hz), 7.26 (d, 1H, J=0.7 Hz), 8.24 (dd, 1H, J=0.7, 1.8 Hz), 8.60 (d, 1H, J=1.8 Hz); MS m/z: 223 (M+H)+, 240 (M+NH4)+ ; Anal. Calcd for C11H11N2OCl.2.0 HCl: C, 44.69; H, 4.43; N, 9.47. Found: C, 44.57; H, 4.31; N, 9.33.

Workup

  1. extractionextracted with CH2Cl2
  2. extractionThe organic extract
  3. dry with materialwas dried over MgSO4
  4. customthe solvent was removed
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 99:1 to 95:5 CHCl3
  7. additionThe product was treated with HCl/ether
  8. customthe salt was recrystallized from EtOH/EtOAc

Sources & evidence

ORD record
ord-88520e76fd5946b8b3e8e0d4c4cb33da
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

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