Trifluoroacetic acid → HCID 88211121, compound

HRID 611570Notes

Reaction equation

HRID 611570 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][C:17]([Cl:22])=[CH:18][CH:19]=2)[CH:14]=1)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[ClH:22].[Cl:22][C:17]1[N:16]=[C:15]2[CH:14]=[C:13]([C@@H:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)[O:21][C:20]2=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 18396228HCID 18396228, compound

Product 1

HCID 88211121HCID 88211121, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 1.5 g sample of the compound from step 11d above was dissolved in 10 mL of CH2Cl2 and cooled to 0° C. The solution was stirred under N2, 10 mL of TFA was added, and the reaction mixture was stirred for 1 hr. The reaction mixture was poured into saturated K2CO3, and the mixture was extracted with CH2Cl2. The solution 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 residue was converted to the salt by treatment with HCl/ether to give 0.78 g of title compound: 1H NMR (D2O, 300 MHz) δ 2.22-2.65 (m, 4H), 3.52-3.57 (m, 2H), 5.06 (t, 1H, J=8 Hz), 7.15 (d, 1H), 7.48 (d, 1H, J=8.6 Hz), 8.1 (d, 1H, J=8.6 Hz); MS m/z: 223 (M+H)+, 240 (M+NH4)+ ; Anal. Calcd for C11H11N2OCl.1.0 HCl: C, 50.99; H, 4.67 N, 10.81. Found: C, 51.21; H, 4.79; N, 10.55.

Workup

  1. stirringthe reaction mixture was stirred for 1 hr
  2. extractionthe mixture was extracted with CH2Cl2
  3. dry with materialThe solution was 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

Sources & evidence

ORD record
ord-43761bb13b6b4bc9922c91ddf9089917
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

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