Trifluoroacetic acid → HCID 71293513, compound

HRID 1402590Notes

Reaction equation

HRID 1402590 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:44]=[CH:43][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][NH:35]C(=O)OC(C)(C)C)=[O:30])[CH:25]=3)[CH:19]=2)=[CH:15][CH:14]=1)=[O:11].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:35][CH2:34][CH2:33][CH2:32][NH:31][C:29]([C:26]1[CH:25]=[C:24]([C:20]2[CH:19]=[C:18]([O:17][C:16]3[CH:15]=[CH:14][C:13]([NH:12][C:10]([NH:9][C:3]4[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=4[F:1])=[O:11])=[CH:44][CH:43]=3)[CH:23]=[CH:22][N:21]=2)[NH:28][CH:27]=1)=[O:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86678335HCID 86678335, compound

Product 1

HCID 71293513HCID 71293513, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of tert-butyl (3-{[(5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3-yl)carbonyl]amino}propyl)carbamate (70 mg, 0.12 mmol) in 10 ml of methylene chloride was added 1 ml of trifluoroacetic acid. The mixture was stirred at room temperature for 2 hours 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-(3-aminopropyl)-5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrole-3-carboxamide as yellow solid. Yield: 40 mg, 63%.

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-d5a68b65c65149c78024911489ea47ac
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

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