Phenyl 3-isopropylisoxazol-5-ylcarbamate → Phenyl 3-(2-cyanopropan-2-yl)isoxazol-5-ylcarbamate

HRID 1917855Notes

Reaction equation

HRID 1917855 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([C:7]([CH3:11])([CH3:10])[C:8]#[N:9])[CH:3]=1.C(C1C=C(N[C:21](=[O:29])[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)ON=1)(C)C>>[C:8]([C:7]([C:4]1[CH:3]=[C:2]([NH:1][C:21](=[O:29])[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:6][N:5]=1)([CH3:11])[CH3:10])#[N:9]

Participants

3

Reactant 2

HCID 13489689Phenyl 3-isopropylisoxazol-5-ylcarbamateHCID 668766082-(5-Aminoisoxazol-3-yl)-2-methylpropanenitrile

Product 1

HCID 66877010Phenyl 3-(2-cyanopropan-2-yl)isoxazol-5-ylcarbamateYield 40%

Procedure

Prepared from 2-(5-aminoisoxazol-3-yl)-2-methylpropanenitrile (130 mg, 0.861 mmol) according to the method described for phenyl 3-isopropylisoxazol-5-ylcarbamate in Example 122A Step 3, to afford phenyl 3-(2-cyanopropan-2-yl)isoxazol-5-ylcarbamate as a colorless solid (93 mg, 40%). 1H NMR (300 MHz, CDCl3) δ 7.82 (brs, 1H), 7.41-7.46 (m, 2H), 7.32 (m, 1H), 7.18-7.21 (m, 2H), 6.29 (s, 1H), 1.83 (s, 6H); LC-MS (ESI) m/z 272 (M+H)+.

Sources & evidence

ORD record
ord-1bbb614815674218971ee08daeda60ec
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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