2-Chlorobenzoyl chloride → HCID 67359726, compound

HRID 60549Notes

Reaction equation

HRID 60549 reaction equation
[CH:1]1([CH:6]2[O:10][B:9]([OH:11])[C:8]3[CH:12]=[C:13]([NH:16]C(=O)C4C=CC=CC=4C(F)(F)F)[CH:14]=[CH:15][C:7]2=3)[CH2:5][CH2:4]CC1.[Cl:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](Cl)=[O:33].[CH2:39]([Mg]Br)C(C)C>>[Cl:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([NH:16][C:13]1[CH:14]=[CH:15][C:7]2[CH:6]([CH2:1][CH:5]([CH3:4])[CH3:39])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=1)=[O:33]

Participants

4

Reactant 3

HCID 691102-Chlorobenzoyl chlorideHCID 66927470N-(3-Cyclopentyl-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-2-trifluoromethyl-benzamideHCID 178418816HCID 178418816, compound

Product 1

HCID 67359726HCID 67359726, compound

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 2-chlorobenzoyl chloride replacing 2-trifluoromethylbenzoyl chloride, and with isobutyl magnesium bromide replacing cyclopentyl magnesium bromide. Data: LCMS (M/Z): 344 (M+H); 1H NMR (DMSO-d6) δ: 10.47 (s, 1H), 9.13 (s, 1H), 8.07 (d, J=1.8 Hz, 1H), 7.66 (dd, J=8.2, 2.0 Hz, 1H), 7.51-7.55 (m, 1H), 7.38-7.50 (m, 2H), 7.30 (d, J=8.2 Hz, 1H), 5.10 (dd, J=9.8, 3.0 Hz, 1H), 1.79-1.92 (m, 1H), 1.65 (ddd, J=13.8, 9.0, 3.1 Hz, 1H), 1.26 (ddd, J=14.0, 9.7, 4.7 Hz, 1H), 0.98 (d, J=6.5 Hz, 3H), 0.89 (d, J=6.7 Hz, 3H).

Sources & evidence

ORD record
ord-3bed32318d004c9e89c202a70a46094b
Source dataset
uspto-grants-2016_09
Patent number
US09440994B2

Reaction notes

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