Trifluoroacetic acid → HCID 73848569, compound

HRID 618789Notes

Reaction equation

HRID 618789 reaction equation
C(OC(=O)[C:7]([C:36]#[N:37])=[C:8]([NH:21][C:22]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=1)[NH:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=[O:20])(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:30][C:28]([F:29])([F:31])[C:26]1[CH:27]=[C:22]([NH:21][C:8]([NH:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]2=[O:20])=[CH:7][C:36]#[N:37])[CH:23]=[C:24]([C:32]([F:35])([F:33])[F:34])[CH:25]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86754513HCID 86754513, compound

Product 1

HCID 73848569HCID 73848569, compoundYield 114.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[3,5-bis(trifluoromethyl)phenylamino]-2-cyano-3-[3-(2-oxoazepan-1-yl)propylamino]acrylic acid tert-butyl ester (203 mg, 0.37 mmol) in DCM (6.0 mL) at 0° C. TFA (6.0 mL) was added. The resulting mixture was stirred at 0° C. for 30 min and then poured into an ice-cold, aqueous, saturated NaHCO3 -solution (100 mL). After dilution with DCM (30 mL) phases were separated, the aqueous layer was extracted (3×20 mL DCM), the combined extracts were washed with brine (2×50 mL), dried (magnesium sulfate) and concentrated, to yield 190 mg (100%) of the title compound as an oil (mixture of isomers). LCMS: elution at 9.97 min, MH+ : 449). 1H NMR (300 MHz, DMSO-d6): δ=1.45-1.80 (m, 8H), 2.40 (m, 2H), 2.95 (m, 1H), 3.21 (m, 2H), 3.35 (m, 6H), 3.58 (s, br, 1H), 7.35-7.70 (m, 3H).

Workup

  1. customat 0° C
  2. customAfter dilution with DCM (30 mL) phases were separated
  3. extractionthe aqueous layer was extracted (3×20 mL DCM)
  4. washthe combined extracts were washed with brine (2×50 mL)
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-da57c30979724f8e99eeb6de1ab3ebd8
Source dataset
uspto-grants-1999_09
Patent number
US05955548

Reaction notes

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