Trifluoroacetic acid → HCID 71499119, compound

HRID 571833Notes

Reaction equation

HRID 571833 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]3[CH:24]=[N:25][C:26]([Cl:29])=[CH:27][CH:28]=3)=[O:21])=[C:15]([Cl:30])[CH:14]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[Cl:29][C:26]1[N:25]=[CH:24][C:23]([NH:22][C:20]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([CH:10]3[CH2:11][CH2:12][NH:8][CH2:9]3)=[CH:14][C:15]=2[Cl:30])=[O:21])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86674690HCID 86674690, compound

Product 1

HCID 71499119HCID 71499119, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of (RS)-3-{3-chloro-4-[3-(6-chloro-pyridin-3-yl)-ureido]-phenyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (68 mg) in dichloromethane (6 ml) was added trifluoroacetic acid (92 μl) and the reaction mixture was then stirred at room temperature for 34 h. The reaction mixture was then 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 (RS)-1-(6-chloro-pyridin-3-yl)-3-(2-chloro-4-pyrrolidin-3-yl-phenyl)-urea (9 mg, 17%) as an off-white solid. MS (ISP): 355.1 ([{37Cl}M+H]+), 353.1 ([{37Cl35Cl}M+H]+), 351.2 ([{35Cl}M+H]+).

Workup

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

Sources & evidence

ORD record
ord-864333e9e0f4491fa5044669fab87f1c
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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