Trifluoroacetic acid → HCID 67168593, compound

HRID 872818Notes

Reaction equation

HRID 872818 reaction equation
[Cl:1][C:2]1[C:3]([CH3:25])=[C:4]([C:10]2[CH:14]=[C:13]([CH2:15][CH2:16][NH:17]C(=O)OC(C)(C)C)[O:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:17][CH2:16][CH2:15][C:13]1[O:12][N:11]=[C:10]([C:4]2[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:2]([Cl:1])[C:3]=2[CH3:25])[CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 123912097HCID 123912097, compound

Product 1

HCID 67168593HCID 67168593, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (2-(3-(3-chloro-4-cyano-2-methylphenyl)isoxazol-5-yl)ethyl)-carbamate (0.56 g, 1.55 mmol) was dissolved to DCM (20 ml). To this mixture was added TFA (1.15 ml) and stirred at RT overnight. The reaction mixture was evaporated to dryness and dissolved to diethyl ether. 1 M HCl in diethyl ether solution was added and the mixture was stirred at RT for 2 h. The HCl salt of the title compound (0.20 g) was filtered and dried. 1H-NMR (400 MHz; d6-DMSO): δ 2.50 (s, 3H), 2.92 (m, 2H), 3.22 (m, 2H), 6.88 (s, 1H), 7.65 (d, 1H), 7.98 (d, 1H), 8.23 (bs, 3H).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutiondissolved to diethyl ether
  3. addition1 M HCl in diethyl ether solution was added
  4. stirringthe mixture was stirred at RT for 2 h
  5. filtrationThe HCl salt of the title compound (0.20 g) was filtered
  6. customdried

Sources & evidence

ORD record
ord-c0e30ebd436346b198344882029eda5d
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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