Trifluoroacetic acid → HCID 90411403, compound

HRID 1521985Notes

Reaction equation

HRID 1521985 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:15][C:16]([C:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH:19]=3)=[CH:17][C:10]=12.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:15][C:16]([C:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH:19]=3)=[CH:17][C:10]=12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90411607HCID 90411607, compound

Product 1

HCID 90411403HCID 90411403, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 222B (0.255 g, 0.620 mmol) in dichloromethane (5 mL) was treated with trifluoroacetic acid (0.477 mL, 6.20 mmol) and the mixture was stirred for 3 hours and concentrated. The residue was dissolved in 2 mL methanol and treated slowly with 2 mL 2M hydrogen chloride in ether. The suspension was diluted with ether and stirred for 10 minutes. The solids were filtered, washed with ether, and dried to give the title compound as a hydrochloride salt. MS (ESI+) m/z 312.1 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in 2 mL methanol
  3. additiontreated slowly with 2 mL 2M hydrogen chloride in ether
  4. additionThe suspension was diluted with ether
  5. stirringstirred for 10 minutes
  6. filtrationThe solids were filtered
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-f6b23094e6f4484786a20e6a80a2dbed
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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