Trifluoroacetic acid → HCID 68325568, compound

HRID 2403287Notes

Reaction equation

HRID 2403287 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[O:27][CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23]3)=[CH:18][C:17]=2[CH3:35])=[N:13][CH:14]=1.CCOC(C)=O.C1COCC1>O.C(#N)C>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[O:27][CH2:26][CH2:25][NH:24][CH2:23]3)=[CH:18][C:17]=2[CH3:35])=[N:13][CH:14]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21939870Tetrahydrofuran ethyl acetateHCID 68327931HCID 68327931, compound

Product 1

HCID 68325568HCID 68325568, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of trifluoroacetic acid (67.0 μl) in water (6 ml) was added a solution of tert-butyl (RS)-2-(4-(5-bromopyridin-2-ylamino)-3-methylphenyl)morpholine-4-carboxylate (39 mg) in acetonitrile (2 ml). The reaction mixture was then capped and the mixture was shaken at 80° C. for 2 h. The reaction mixture was then cooled to room temperature and poured into EtOAc/THF (1:1) and washed with 1 M aq. NaOH. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash column chromatography (Isolute® Flash-NH2 from Separtis; gradient: heptane/EtOAc/MeOH) to afford (RS)-5-bromo-N-(2-methyl-4-(morpholin-2-yl)phenyl)pyridin-2-amine (17 mg, 56%) as a light yellow amorphous solid. MS (ISP): 350.1 ([{81Br}M+H]+), 348.2 ([{79Br}M+H]+).

Workup

  1. customThe reaction mixture was then capped
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. washwashed with 1 M aq. NaOH
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash column chromatography (Isolute® Flash-NH2 from Separtis; gradient: heptane/EtOAc/MeOH)

Sources & evidence

ORD record
ord-10cbd7ee78b3442387a985798376da89
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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