Trifluoroacetic acid → HCID 68325559, compound

HRID 2403311Notes

Reaction equation

HRID 2403311 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[N:14]=[CH:13][C:12]([CH:15]3[O:20][CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]3)=[CH:11][C:10]=2[CH3:28])=[N:6][CH:7]=1.FC(F)(F)C(O)=O.CCOC(C)=O.C1COCC1>C(#N)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[C:10]([CH3:28])=[CH:11][C:12]([CH:15]3[O:20][CH2:19][CH2:18][NH:17][CH2:16]3)=[CH:13][N:14]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21939870Tetrahydrofuran ethyl acetateHCID 86671404HCID 86671404, compound

Product 1

HCID 68325559HCID 68325559, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of tert-butyl (RS)-2-(6-(5-bromopyridin-2-ylamino)-5-methylpyridin-3-yl)morpholine-4-carboxylate (26 mg) in acetonitrile (1.5 ml) and water (4.5 ml) was added trifluoroacetic acid (45 μl). The reaction mixture was then capped and the mixture was shaken at 80° C. for 3 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)—N-(5-bromopyridin-2-yl)-3-methyl-5-(morpholin-2-yl)pyridin-2-amine (11 mg, 54%) as a colourless amorphous solid. MS (ISP): 351.1 ([{81Br}M+H]+), 349.1 ([{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-4ba30c0d918c412ab0568d649a7b01a3
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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