Trifluoroacetic acid → HCID 68491403, compound

HRID 2069185Notes

Reaction equation

HRID 2069185 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:10][CH:9]2[NH:11]C(=O)OCCCC)[CH:5]=[CH:6][CH:7]=1.[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22]>C(Cl)Cl>[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22].[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:10][CH:9]2[NH2:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86643591HCID 86643591, compound

Product 1

HCID 68491403HCID 68491403, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9 (560 mg, 2.2 mmol) in CH2Cl2 (15 mL) was added trifluoroacetic acid (15 mL). The reaction mixture was stirred at room temperature for 30 min. The solvent was removed by rotary evaporation. The yellow oil was put under vacuum for 24 h to give crude amine 4b (579 mg, 2.2 mmol, 100%) as a yellow oil, which was used in the next step without further purification: 1H NMR (500 MHz, CDCl3) δ 1.10-1.30 (br s, 1H), 1.40-1.60 (br s, 1H), 2.30-2.50 (br s, 1H), 2.70-2.90 (br s, 1H), 6.70-6.72 (m, 1H), 6.72-6.77 (m, 1H), 6.89-7.00 (m, 1H), 7.10-7.30 (m, 1H), 7.80-8.20 (br s, 2H), 10.8-11.8 (br s, 1H); 13C NMR (125 MHz, CDCl3) δ 13.2, 21.5, 31.6, 113.5, 113.7, 114.2, 114.4, 122.29, 122.31, 130.4, 130.5, 140.1, 140.2, 162.2, 164.1; LCQ-MS (M+H+) calcd for C9H11FN 152. found 152; LC-TOF (M+H+) calcd for C9H11FN 152.08755. found 152.08703.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. waitThe yellow oil was put under vacuum for 24 h

Sources & evidence

ORD record
ord-7ea981356d144f419a07326752cdfeed
Source dataset
uspto-grants-2012_10
Patent number
US08299100B2

Reaction notes

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