Trifluoroacetic acid → 1-{3-[({7-[3-Fluoro-4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]thieno[3,2-b]pyridin-2-yl}carbonyl)amino]propyl}pyrrolidine-3-carboxylic acid

HRID 525819Notes

Reaction equation

HRID 525819 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[NH:36][C:37]([NH:39][C:40]1[CH:45]=[C:44]([CH3:46])[CH:43]=[CH:42][C:41]=1[F:47])=[O:38])[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][CH2:20][N:21]3[CH2:25][CH2:24][CH:23]([C:26]([O:28]C(C)(C)C)=[O:27])[CH2:22]3)=[O:16])[S:14][C:7]=12.FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[NH:36][C:37]([NH:39][C:40]1[CH:45]=[C:44]([CH3:46])[CH:43]=[CH:42][C:41]=1[F:47])=[O:38])[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][CH2:20][N:21]3[CH2:25][CH2:24][CH:23]([C:26]([OH:28])=[O:27])[CH2:22]3)=[O:16])[S:14][C:7]=12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86290928HCID 86290928, compound

Product 1

HCID 862908871-{3-[({7-[3-Fluoro-4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]thieno[3,2-b]pyridin-2-yl}carbonyl)amino]propyl}pyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 1-{3-[({7-[3-fluoro-4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]thieno[3,2-b]pyridin-2-yl}carbonyl)amino]propyl}pyrrolidine-3-carboxylate (40 mg, 0.060 mmol) in 5 ml of methylene chloride was added 2 ml of trifluoroacetic acid. The mixture was stirred at room temperature for 2 hours, and evaporated to dryness under reduced pressure. 5 ml of water was added to the residue, and the mixture was neutralized to pH=7 with saturated NaHCO3 solution with vigorous stirring. The precipitates were filtered, washed with 5 ml of water, and dried in vacuo to give 1-{3-[({7-[3-fluoro-4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]thieno[3,2-b]pyridin-2-yl}carbonyl)amino]propyl}pyrrolidine-3-carboxylic acid as light brown solid. Yield: 37 mg, 100%.

Workup

  1. customevaporated to dryness under reduced pressure
  2. addition5 ml of water was added to the residue
  3. filtrationThe precipitates were filtered
  4. washwashed with 5 ml of water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-edbeeb8bfcad4eed962e3164e1874061
Source dataset
uspto-grants-2016_05
Patent number
US09340555B2

Reaction notes

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