2,1-Benzoxazol-3-amine → N-2,1-benzisoxazol-3-yl-4-(3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}benzylidene)piperidine-1-carboxamide

HRID 1666332Notes

Reaction equation

HRID 1666332 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5](=[CH:8][C:9]2[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=2)[O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=2)[CH2:4][CH2:3]1.[N:26]1[O:27][C:28]([NH:35][C:36](=O)[O:37]C2C=CC=CC=2)=[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=12.NC1ON=C2C=CC=CC=12>>[N:26]1[O:27][C:28]([NH:35][C:36]([N:2]2[CH2:7][CH2:6][C:5](=[CH:8][C:9]3[CH:25]=[CH:24][CH:23]=[C:11]([O:12][C:13]4[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:15][N:14]=4)[CH:10]=3)[CH2:4][CH2:3]2)=[O:37])=[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=12

Participants

4

Reactant 3

HCID 552809832,1-Benzoxazol-3-amineHCID 66876060Phenyl benzo[c]isoxazol-3-ylcarbamateHCID 668761612-(3-(Piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine hydrochloride

Product 1

HCID 24967992N-2,1-benzisoxazol-3-yl-4-(3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}benzylidene)piperidine-1-carboxamide

Procedure

Following the procedure in Example 1, Step 6, 2-(3-piperidin-4-ylidenemethyl-phenoxy)-5-trifluoromethyl-pyridine hydrochloride (150 mg, 0.40 mmol, from Example 1, Step 5) and phenyl benzo[c]isoxazol-3-ylcarbamate (113 mg, 0.40 mmol, prepared according to the procedure described in Synthesis, 1997, 1189-1194 from 3-amino-2,1-benzisoxazole) were combined to provide the title compound (168 mg). MS (APCI 10V) AP+ 495.2, 376.2, 335.2; 1H NMR (400 MHz, CD3OD) δ ppm 2.56 (dt, J=50.88, 5.69 Hz, 4H) 3.66 (dt, J=37.31, 5.71 Hz, 4H) 6.48 (s, 1H) 6.98-7.07 (m, 2H) 7.13 (ddd, J=8.75, 0.68, 0.56 Hz, 1H) 7.16 (d, J=7.77 Hz, 1H) 7.30 (ddd, J=8.05, 6.80, 1.16 Hz, 1H) 7.41 (t, J=7.99 Hz, 1H) 7.49-7.66 (m, 2H) 7.85 (dt, J=8.13, 1.03 Hz, 1H) 8.09 (ddd, J=8.72, 2.67, 0.38 Hz, 1H) 8.43 (td, J=1.82, 0.93 Hz, 1H).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-0e16de5316d34d26b509a93d3b276053
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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