Trifluoroacetic acid → HCID 118061992, compound

HRID 920719Notes

Reaction equation

HRID 920719 reaction equation
[C:1]([C:4]1[C:5]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=2)=[N:6][N:7]2[CH2:12][CH2:11][N:10]([C:13]([NH:15][CH:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)=[O:14])[CH2:9][C:8]=12)(=[O:3])[NH2:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:35][C:31]1[CH:30]=[C:29]([C:5]2[C:4]([C:1]([NH2:2])=[O:3])=[C:8]3[CH2:9][N:10]([C:13]([NH:15][CH:16]4[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]4)=[O:14])[CH2:11][CH2:12][N:7]3[N:6]=2)[CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118069204HCID 118069204, compound

Product 1

HCID 118061992HCID 118061992, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 97A (300 mg, 0.617 mmol) in DCM (3 mL) was added TFA (0.238 mL, 3.08 mmol) at 0° C. and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was concentrated and the resultant residue was basified to pH=8.0 with 10% NaHCO3 solution. The aqueous layer was extracted with DCM (3×5 mL) and the combined organic layer was washed with water (2×5 mL), brine, dried over Na2SO4, filtered and concentrated to afford Intermediate 97B (200 mg, 80%) as white solid. MS(ES): m/z=387 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.50 (bs, 1H), 7.46 (m, 3H), 7.32 (bs, 1H), 7.21 (m, 1H), 7.11 (bs, 1H), 6.86 (d, J=7.03 Hz, 1H), 4.74 (s, 2H), 4.15 (t, J=5.27 Hz, 2H), 3.86 (t, J=5.27 Hz, 2H), 3.72 (m, 1H), 3.27 (s, 2H), 2.96 (m, 2H), 1.93 (m, 2H), 1.54 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionThe aqueous layer was extracted with DCM (3×5 mL)
  3. washthe combined organic layer was washed with water (2×5 mL), brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c411e8e1091943beb31e88c9a018f87d
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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