HCID 86625259, compound → HCID 178461558, compound

HRID 2424417Notes

Reaction equation

HRID 2424417 reaction equation
[CH3:1][C@H:2]1[N:7]([C:8](=[O:13])[C:9]([F:12])([F:11])[F:10])[C@@H:6]([CH3:14])[CH2:5][N:4]([CH2:15][C:16]2[CH:20]=[CH:19][N:18](C(OC(C)(C)C)=O)[N:17]=2)[CH2:3]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:15][C:16]2[CH:20]=[CH:19][NH:18][N:17]=2)[CH2:5][C@H:6]([CH3:14])[N:7]1[C:8](=[O:13])[C:9]([F:10])([F:12])[F:11]

Participants

4

Reactant 1

HCID 86625259HCID 86625259, compound

Product 1

HCID 178461558HCID 178461558, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
25 °C

Procedure

D8 (2.20 g, 5.63 mmol) was taken up in 25% TFA in DCM (50 ml) and stirred for 4 h at 25° C. The solvent was removed in vacuo and the residue dissolved in DCM (50 ml), washed with saturated NaHCO3, dried (Na2SO4) and concentrated to yield the title compound as an orange foam (1.64 g). δH (CDCl3) 1.43 (6H, d), 2.48 (2H, dd), 2.97 (2H, d), 3.88 (2H, s), 4.15-4.75 (2H, br d), 6.40 (1H, d), 7.64 (1H, d), 8.93 (1H, br s). MS (ES): MH+ 291.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in DCM (50 ml)
  3. washwashed with saturated NaHCO3
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-418fb3b5504546599f7f2896a370862a
Source dataset
uspto-grants-2011_06
Patent number
US07964602B2

Reaction notes

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