N-(3-Cyclopentyl-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-2-trifluoromethyl-benzamide → N-(1-Hydroxy-3-isobutyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-2-trifluoromethyl-benzamide

HRID 60546Notes

Reaction equation

HRID 60546 reaction equation
[CH:1]1([CH:6]2[O:10][B:9]([OH:11])[C:8]3[CH:12]=[C:13]([NH:16][C:17](=[O:28])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:24]([F:27])([F:26])[F:25])[CH:14]=[CH:15][C:7]2=3)[CH2:5][CH2:4]CC1.[CH2:29]([Mg]Br)C(C)C>>[OH:11][B:9]1[C:8]2[CH:12]=[C:13]([NH:16][C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:26])([F:27])[F:25])[CH:14]=[CH:15][C:7]=2[CH:6]([CH2:1][CH:5]([CH3:4])[CH3:29])[O:10]1

Participants

3

Reactant 2

HCID 66927470N-(3-Cyclopentyl-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-2-trifluoromethyl-benzamideHCID 178418816HCID 178418816, compound

Product 1

HCID 67358742N-(1-Hydroxy-3-isobutyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-2-trifluoromethyl-benzamide

Procedure

The title compound was prepared using a procedure similar to that of N-(3-cyclopentyl-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-2-trifluoromethyl-benzamide with isobutyl magnesium bromide replacing cyclopentyl magnesium bromide. Data: LCMS (M/Z): 378 (M+H); 1H NMR (DMSO-d6) δ: 10.53 (s, 1H), 9.13 (s, 1H), 8.06 (d, J=1.9 Hz, 1H), 7.81 (d, J=7.5 Hz, 1H), 7.73-7.79 (m, 1H), 7.65-7.71 (m, 2H), 7.62 (dd, J=8.2, 2.0 Hz, 1H), 7.31 (d, J=8.2 Hz, 1H), 5.10 (dd, J=9.8, 3.0 Hz, 1H), 1.81-1.92 (m, 1H), 1.65 (ddd, J=13.9, 9.0, 3.1 Hz, 1H), 1.27 (ddd, J=14.1, 9.7, 4.6 Hz, 1H), 0.98 (d, J=6.6 Hz, 3H), 0.89 (d, J=6.7 Hz, 3H).

Sources & evidence

ORD record
ord-c1f61bcc9b6f43d2b92476ad2458022a
Source dataset
uspto-grants-2016_09
Patent number
US09440994B2

Reaction notes

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