Trifluoroacetic acid → HCID 90413908, compound

HRID 1521968Notes

Reaction equation

HRID 1521968 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:30][CH3:31])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([CH:17]4[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]4)=[CH:16][C:9]=23)[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:30][CH3:31])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([CH:17]4[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]4)=[CH:16][C:9]=23)[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90412965HCID 90412965, compound

Product 1

HCID 90413908HCID 90413908, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 135A (0.955 g, 2.24 mmol) in dichloromethane (20 mL) was treated with trifluoroacetic acid (1.73 mL, 22.4 mmol) and the mixture was stirred for 3 hours. After concentration, the residue was dissolved in 10 mL methanol and treated with 30 mL 1M hydrogen chloride in ether. After stirring for 15 minutes, the mixture was treated with ether and the solids were filtered, washed with ether and oven-dried to afford the title compound as a hydrochloride salt. MS (ESI+) m/z 326.1 (M+H)+.

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved in 10 mL methanol
  3. additiontreated with 30 mL 1M hydrogen chloride in ether
  4. stirringAfter stirring for 15 minutes
  5. additionthe mixture was treated with ether
  6. filtrationthe solids were filtered
  7. washwashed with ether
  8. customoven-dried

Sources & evidence

ORD record
ord-c16f3af67fe84a6f8a37bc887b9678a6
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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