tert-Butyl (2-(3-(3-chloro-4-cyanophenyl)isoxazol-5-yl)ethyl)carbamate → 4-(5-(2-Aminoethyl)isoxazol-3-yl)-2-chlorobenzonitrile hydrochloride

HRID 872832Notes

Reaction equation

HRID 872832 reaction equation
[Cl:1][C:2]1[CH:3]=[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]>Cl.C(OC(=O)C)C>[ClH:1].[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])[CH:3]=2)[CH:14]=1

Participants

3

Reactant 1

HCID 131732550tert-Butyl (2-(3-(3-chloro-4-cyanophenyl)isoxazol-5-yl)ethyl)carbamate

Product 1

HCID 671683064-(5-(2-Aminoethyl)isoxazol-3-yl)-2-chlorobenzonitrile hydrochlorideYield 166.5%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

tert-Butyl (2-(3-(3-chloro-4-cyanophenyl)isoxazol-5-yl)ethyl)carbamate (078 g, 2.24 mmol) was stirred with 13 w-% ethylacetate HCl solution (20 ml) for 2 h at RT. The mixture was filtered and the precipitate was washed with EtOAc, dried in vacuo at 30° C. overnight. The title compound 0.53 g was obtained. 1H-NMR (400 MHz; d6-DMSO): δ 3.21 (m, 4H), 7.22 (s, 1H), 8.02 (d, 1H), 8.14 (d, 1H), 8.20 (s, 1H), 8.27 (bs, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. washthe precipitate was washed with EtOAc
  3. customdried in vacuo at 30° C. overnight

Sources & evidence

ORD record
ord-06e2d3160efb420b900c9a0c084e8f54
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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