Trifluoroacetic acid → HCID 58043655, compound

HRID 1919053Notes

Reaction equation

HRID 1919053 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[CH:15][C:14]([O:17][CH:18]3[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]3)=[CH:13][CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:20]1[CH2:21][CH:18]([O:17][C:14]2[CH:13]=[CH:12][C:11]([NH:10][C:4]3[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=[C:2]([Br:1])[CH:3]=3)=[N:16][CH:15]=2)[CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58043697tert-Butyl 3-(6-(5-Bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-3-yloxy)azetidine-1-carboxylate

Product 1

HCID 58043655HCID 58043655, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 251c (1.14 g, 3.10 mmol), methylene chloride (10 mL) and trifluoroacetic acid (5 mL). The reaction mixture was stirred at room temperature for 2 h. After this time, the mixture was concentrated under reduced pressure. The resulting residue was diluted with methylene chloride (100 mL) and washed with saturated aqueous sodium bicarbonate (50 mL). The aqueous layer was extracted with methylene chloride (2×50 mL) and the combined organic extracts were dried over sodium sulfate, filtered and concentrated to afford a 92% yield (1.10 g) of 251d as a colorless oil. This compound was used directly for the next step without any purification: 1H NMR (500 MHz, DMSO-d6) d 8.65 (s, 1H), 8.55 (d, 1H, J=2.5 Hz), 7.82 (d, 1H, J=3.0 Hz), 7.48 (d, 1H, J=2.5 Hz), 7.30 (d, 1H, J=9.0 Hz), 7.21 (m, 1H), 4.95 (t, 1H, J=6.0 Hz), 3.76 (m, 1H), 3.48 (m, 5H); MS (ESI+) m/z 353.0 (M+H).

Workup

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. concentrationAfter this time, the mixture was concentrated under reduced pressure
  3. additionThe resulting residue was diluted with methylene chloride (100 mL)
  4. washwashed with saturated aqueous sodium bicarbonate (50 mL)
  5. extractionThe aqueous layer was extracted with methylene chloride (2×50 mL)
  6. dry with materialthe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-646ec43a0041466c9a5e808974b33da8
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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