Phenyl 3-isopropylisoxazol-5-ylcarbamate → phenyl 3-(tetrahydro-2H-pyran-4-yl)isoxazol-5-ylcarbamate

HRID 631405Notes

Reaction equation

HRID 631405 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:11]=[C:10]([NH2:12])[O:9][N:8]=2)[CH2:3][CH2:2]1.C(C1C=C(N[C:22](=[O:30])[O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)ON=1)(C)C>>[O:1]1[CH2:2][CH2:3][CH:4]([C:7]2[CH:11]=[C:10]([NH:12][C:22](=[O:30])[O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:9][N:8]=2)[CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 13489689Phenyl 3-isopropylisoxazol-5-ylcarbamateHCID 592532673-(Oxan-4-yl)-1,2-oxazol-5-amine

Product 1

HCID 66876225phenyl 3-(tetrahydro-2H-pyran-4-yl)isoxazol-5-ylcarbamateYield 56%

Procedure

Prepared from 3-(tetrahydro-2H-pyran-4-yl)isoxazol-5-amine (170 mg, 1.01 mmol) according to the method described for phenyl 3-isopropylisoxazol-5-ylcarbamate in Example 122A Step 3, to afford phenyl 3-(tetrahydro-2H-pyran-4-yl)isoxazol-5-ylcarbamate as a colorless solid (164 mg, 56%). 1H NMR (300 MHz, CDCl3) δ 7.93 (brs, 1H), 7.39-7.45 (m, 2H), 7.18-7.32 (m, 3H), 6.09 (s, 1H), 4.02-4.08 (m, 2H), 3.48-3.57 (m, 2H), 2.96 (m, 1H), 1.78-1.89 (m, 4H); LC-MS (ESI) m/z 289 (M+H)+.

Sources & evidence

ORD record
ord-0f9e7126a4084bcbb16ee466508e8233
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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