Trifluoroacetic acid → HCID 71449747, compound

HRID 1747699Notes

Reaction equation

HRID 1747699 reaction equation
C(OC([N:8]1[CH:12]2[CH2:13][CH2:14][CH:9]1[CH:10]([C:15]1[CH:16]=[N:17][C:18]([F:31])=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)[CH:20]=1)[CH2:11]2)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[NH4+].[OH-]>C(Cl)Cl.O>[CH3:30][S:27]([C:24]1[CH:23]=[CH:22][C:21]([C:19]2[CH:20]=[C:15]([CH:10]3[CH2:11][CH:12]4[NH:8][CH:9]3[CH2:14][CH2:13]4)[CH:16]=[N:17][C:18]=2[F:31])=[CH:26][CH:25]=1)(=[O:28])=[O:29]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 89669920HCID 89669920, compound

Product 1

HCID 71449747HCID 71449747, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 17 (312 mg, 0.7 mmol) was dissolved in anhydrous CH2Cl2 (3 mL) and cooled in an ice-water bath. TFA (3 mL) was added in 30 min. After stirring at room temperature for 1 hr, the mixture was poured into a cold solution of NH4OH in water (1:1). The mixture was then extracted with CH2Cl2. The organic phase was washed with brine, then dried over anhydrous Na2SO4 and evaporated to dryness. After flash chromatography on a silica gel column with CH2Cl2-MeOH, the free base was isolated as a clear oil (242 mg, 99%). 1H NMR (CDCl3): δ (ppm) 1.5-1.7 (m, 5H), 1.8-1.9 (m, 1H), 2.87 (dd, 1H, J=5.1, 9.0 Hz), 3.11 (s, 3H), 3.65 (br s, 1H), 3.84 (m, 1H), 7.7-7.8 (m, 2H), 8.0-8.05 (m, 2H), 8.09 (dd, 1H, J=2.4, 3.6 Hz), 8.15 (m, 1H). 13C NMR (CDCl3): δ (ppm) 29.6, 30.5, 31.7, 40.8, 44.6, 44.9, 56.8, 63.2, 121.6 (d, J=112.5 Hz), 128.0, 130.2 (d, J=12.3 Hz), 140.3 (d, J=14.7 Hz), 141.3 (d, J=18.6 Hz), 146.6 (d, J=57.6 Hz), 157.6, 160.8.

Workup

  1. temperaturecooled in an ice-water bath
  2. extractionThe mixture was then extracted with CH2Cl2
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-78898e7e1ed94861bc99acc2a5f82478
Source dataset
uspto-grants-2015_10
Patent number
US09150581B2

Reaction notes

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