Trifluoroacetic acid → HCID 71499074, compound

HRID 571840Notes

Reaction equation

HRID 571840 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[N:14]=[CH:13][C:12]([NH:15][C:16](=[O:38])[NH:17][C:18]2[CH:23]=[CH:22][C:21]([C@H:24]3[O:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]3)=[CH:20][C:19]=2[CH3:37])=[CH:11][CH:10]=1.[OH-].[Na+]>O.C(#N)C>[Cl:8][C:9]1[N:14]=[CH:13][C:12]([NH:15][C:16]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C@H:24]3[O:29][CH2:28][CH2:27][NH:26][CH2:25]3)=[CH:20][C:19]=2[CH3:37])=[O:38])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86674691HCID 86674691, compound

Product 1

HCID 71499074HCID 71499074, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of trifluoroacetic acid (233 μl) in water (6 ml) was added a solution of (R)-tert-butyl 2-(4-(3-(6-chloropyridin-3-yl)ureido)-3-methylphenyl)morpholine-4-carboxylate (104 mg) in acetonitrile (2 ml). The reaction mixture was then capped and the mixture was shaken at 80° C. for 4 h. The reaction mixture was then cooled to room temperature and poured into 1 M aq. NaOH and the resulting mixture was extracted twice with EtOAc. The organic layers were 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 (R)-1-(6-chloropyridin-3-yl)-3-(2-methyl-4-(morpholin-2-yl)phenyl)urea (41 mg, 51%) as a white solid. MS (ISP): 349.1 ([{37Cl}M+H]+), 347.1 ([{35Cl}M+H]+).

Workup

  1. customThe reaction mixture was then capped
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. extractionthe resulting mixture was extracted twice with EtOAc
  4. dry with materialThe organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash column chromatography (Isolute® Flash-NH2 from Separtis)

Sources & evidence

ORD record
ord-dc6e038c62904ac0bb731b9d239547d2
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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