Trifluoroacetic acid → 5-(ethylamino)-4-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]-5-oxopentanoic acid

HRID 1402594Notes

Reaction equation

HRID 1402594 reaction equation
[CH2:1]([NH:3][C:4](=[O:48])[CH:5]([NH:15][C:16]([C:18]1[CH:22]=[C:21]([C:23]2[CH:28]=[C:27]([O:29][C:30]3[CH:35]=[C:34]([C:36]([NH:38][C:39]4[CH:44]=[C:43]([CH3:45])[CH:42]=[CH:41][C:40]=4[F:46])=[O:37])[CH:33]=[CH:32][C:31]=3[F:47])[CH:26]=[CH:25][N:24]=2)[NH:20][CH:19]=1)=[O:17])[CH2:6][CH2:7][C:8]([O:10]C(C)(C)C)=[O:9])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([NH:3][C:4](=[O:48])[CH:5]([NH:15][C:16]([C:18]1[CH:22]=[C:21]([C:23]2[CH:28]=[C:27]([O:29][C:30]3[CH:35]=[C:34]([C:36]([NH:38][C:39]4[CH:44]=[C:43]([CH3:45])[CH:42]=[CH:41][C:40]=4[F:46])=[O:37])[CH:33]=[CH:32][C:31]=3[F:47])[CH:26]=[CH:25][N:24]=2)[NH:20][CH:19]=1)=[O:17])[CH2:6][CH2:7][C:8]([OH:10])=[O:9])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71293530tert-butyl 5-(ethylamino)-4-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]-5-oxopentanoate

Product 1

HCID 712935915-(ethylamino)-4-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]-5-oxopentanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 5-(ethylamino)-4-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]-5-oxopentanoate (75 mg, 0.11 mmol) in 5 ml of methylene chloride was added 1 ml of TFA. The mixture was stirred at room temperature for 90 minutes, and evaporated to dryness under reduced pressure. The residue was re-dissolved in 5 ml of methanol and poured into 100 ml of water with vigorous stirring. The precipitates were filtered, washed with water and dried in vacuo to give 5-(ethylamino)-4-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]-5-oxopentanoic acid as white solid. Yield: 60 mg, 87%.

Workup

  1. customevaporated to dryness under reduced pressure
  2. dissolutionThe residue was re-dissolved in 5 ml of methanol
  3. additionpoured into 100 ml of water with vigorous stirring
  4. filtrationThe precipitates were filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a1015fe5fd854288a9887619239828d4
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

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