Trifluoroacetic acid → HCID 86290749, compound

HRID 525808Notes

Reaction equation

HRID 525808 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[NH:31][C:32]([NH:34][C:35]1[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][C:36]=1[F:42])=[O:33])[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[CH:12]=[C:13]([C:15]([NH:17][CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)=[O:16])[S:14][C:7]=12.FC(F)(F)C(O)=O>ClCCl>[NH2:20][CH2:19][CH2:18][NH:17][C:15]([C:13]1[S:14][C:7]2[C:8](=[N:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]2[CH:28]=[CH:29][C:30]([NH:31][C:32]([NH:34][C:35]3[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][C:36]=3[F:42])=[O:33])=[C:2]([F:1])[CH:3]=2)[CH:12]=1)=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86290750Tert-butyl {2-[({7-[3-fluoro-4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]thieno[3,2-b]pyridin-2-yl}carbonyl)amino]ethyl}carbamate

Product 1

HCID 86290749HCID 86290749, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of tert-butyl {2-[({7-[3-fluoro-4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]thieno[3,2-b]pyridin-2-yl}carbonyl)amino]ethyl}carbamate (488 mg, 0.82 mmol) in 10 ml of dichloromethane was added 5 ml of trifluoroacetic acid. The mixture was stirred at room temperature for one hour 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)-7-[3-fluoro-4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]thieno[3,2-b]pyridine-2-carboxamide as brown solid. Yield: 400 mg, 99%.

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-18e064163694437991cab37c9d96576c
Source dataset
uspto-grants-2016_05
Patent number
US09340555B2

Reaction notes

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