Trifluoroacetic acid → HCID 71293551, compound

HRID 1402606Notes

Reaction equation

HRID 1402606 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:48]=[CH:47][C:16]([O:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]3[NH:28][CH:27]=[C:26]([C:29]([NH:31][CH2:32][CH2:33][CH2:34][N:35]4[CH2:39][CH2:38][CH:37]([C:40]([O:42]C(C)(C)C)=[O:41])[CH2:36]4)=[O:30])[CH:25]=3)[CH:19]=2)=[CH:15][CH:14]=1)=[O:11].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]3[NH:28][CH:27]=[C:26]([C:29]([NH:31][CH2:32][CH2:33][CH2:34][N:35]4[CH2:39][CH2:38][CH:37]([C:40]([OH:42])=[O:41])[CH2:36]4)=[O:30])[CH:25]=3)[CH:19]=2)=[CH:47][CH:48]=1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71293541HCID 71293541, compound

Product 1

HCID 71293551HCID 71293551, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 1-(3-{[(5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3-yl)carbonyl]amino}propyl)pyrrolidine-3-carboxylate (22 mg, 0.033 mmol) in 2 ml of methylene chloride was added 1 ml of TFA. The mixture was stirred at room temperature for 16 hours, and evaporated to dryness under reduced pressure. The residue was re-dissolved in 2 ml of methanol and poured into 10 ml of water with vigorous stirring. Saturated NaHCO3 solution was added dropwise until pH=7. The precipitates were filtered, washed with water and dried in vacuo to give 1-(3-{[(5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3-yl)carbonyl]amino}propyl)pyrrolidine-3-carboxylic acid as light reddish solid.

Workup

  1. customevaporated to dryness under reduced pressure
  2. dissolutionThe residue was re-dissolved in 2 ml of methanol
  3. additionpoured into 10 ml of water with vigorous stirring
  4. additionSaturated NaHCO3 solution was added dropwise until pH=7
  5. filtrationThe precipitates were filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-f0b1f08e49d9425b9677efb7a8329748
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

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