Trichloroacetyl chloride → 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-imidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

HRID 900254

Reaction equation

[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[C:9]([CH2:12][N:13]3[CH:17]=[CH:16][N:15]=[CH:14]3)[CH:8]=2)=[CH:4][CH:3]=1.CCN(CC)CC.ClC(Cl)(Cl)[C:27](Cl)=[O:28].Cl.Cl.[CH:34]([N:37]1[CH2:42][CH2:41][CH:40]([NH2:43])[CH2:39][CH2:38]1)([CH3:36])[CH3:35]>C(Cl)Cl>[CH:34]([N:37]1[CH2:42][CH2:41][CH:40]([NH:43][C:27]([C:14]2[N:13]([CH2:12][C:9]3[CH:8]=[C:7]([C:5]4[S:6][C:2]([Cl:1])=[CH:3][CH:4]=4)[O:11][N:10]=3)[CH:17]=[CH:16][N:15]=2)=[O:28])[CH2:39][CH2:38]1)([CH3:36])[CH3:35]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-(5-Chloro-thiophen-2-yl)-3-imidazol-1-ylmethyl-isoxazole (85 mg) and NEt3 (89 μL) in DCM (3 mL) was added trichloroacetyl chloride (43 μL) dropwise at 0° C. The mixture was stirred for 5 min at 0° C. and for 30 min at RT. More NEt3 (133 μL) and 1-isopropyl-piperidin-4-ylamine dihydrochloride (88 mg) were added and stirring was continued for 2 h at RT. The mixture was concentrated and the residue was purified by preparative HPLC. The fractions containing the product were evaporated to provide 67 mg of the title compound as its trifluoroacetate salt. MS (ESI+): mi/e=434, chloro pattern.

Workup

stirringstirring
waitwas continued for 2 h at RT
concentrationThe mixture was concentrated
customthe residue was purified by preparative HPLC
additionThe fractions containing the product
customwere evaporated

Sources & evidence

ORD record: ord-855567cfc5f248899cc0bf9c88d2e0b3
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07358268B2

Linked notes

Loading…