Trifluoroacetic acid → N-(2-aminoethyl)-5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrole-3-carboxamide

HRID 1402550Notes

Reaction equation

HRID 1402550 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:30]([C:33]([NH:35][C:36]2[CH:41]=[C:40]([CH3:42])[CH:39]=[CH:38][C:37]=2[F:43])=[O:34])=[CH:29][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[NH:15][CH:14]=[C:13]([C:16]([NH:18][CH2:19][CH2:20][NH:21]C(=O)OC(C)(C)C)=[O:17])[CH:12]=2)[CH:6]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:21][CH2:20][CH2:19][NH:18][C:16]([C:13]1[CH:12]=[C:11]([C:7]2[CH:6]=[C:5]([O:4][C:3]3[CH:29]=[C:30]([C:33]([NH:35][C:36]4[CH:41]=[C:40]([CH3:42])[CH:39]=[CH:38][C:37]=4[F:43])=[O:34])[CH:31]=[CH:32][C:2]=3[F:1])[CH:10]=[CH:9][N:8]=2)[NH:15][CH:14]=1)=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86678330tert-butyl {2-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]ethyl}carbamate

Product 1

HCID 71293631N-(2-aminoethyl)-5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of tert-butyl {2-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]ethyl}carbamate (360 mg, 0.61 mmol) in 5 ml of methylene chloride was added 3 ml of trifluoroacetic acid. The mixture was stirred at room temperature for 20 minutes and evaporated to dryness under reduced pressure. The residue was re-dissolved in MeOH (5 ml) and poured into 100 ml of water with vigorous stirring. Saturated NaHCO3 solution was added until pH=8-9. The precipitates were filtered, washed with water and dried in vacuo to give N-(2-aminoethyl)-5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrole-3-carboxamide as beige solid. Yield: 280 mg, 94%.

Workup

  1. customevaporated to dryness under reduced pressure
  2. dissolutionThe residue was re-dissolved in MeOH (5 ml)
  3. additionpoured into 100 ml of water with vigorous stirring
  4. additionSaturated NaHCO3 solution was added until pH=8-9
  5. filtrationThe precipitates were filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-1a5deddd90fe4a25818c30a25bae8fed
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

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