Hydrochloric Acid → HCID 58789348, compound

HRID 1175610Notes

Reaction equation

[CH2:1]([NH:5][C:6](=[O:24])[C:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:20]([CH3:21])=[CH:19][S:18][CH:17]=2)=[C:12]([O:22]C)[CH:11]=1)([CH3:9])[CH3:8])[CH:2]([CH3:4])[CH3:3].B(Br)(Br)Br.Cl>C(Cl)Cl>[OH:22][C:12]1[CH:11]=[C:10]([C:7]([CH3:8])([CH3:9])[C:6]([NH:5][CH2:1][CH:2]([CH3:3])[CH3:4])=[O:24])[CH:15]=[CH:14][C:13]=1[C:16]1[C:20]([CH3:21])=[CH:19][S:18][CH:17]=1

Participants

Conditions

Temperature: -78 °C

Procedure

N-isobutyl-2-(3-methoxy-4-(4-methylthiophen-3-yl)phenyl)-2-methylpropanamide (example 35a) (103 mg, 0.3 mmol) was dissolved in dry DCM (5 mL), the mixture was under argon cooled to −78° C. and BBr3 (1.69 mL of 1M solution in DCM) was added drop-wise and the mixture was stirred at room temperature for 72 hrs. The solution was diluted with DCM and treated with 1M aq. HCl. The organic phase was washed with water and brine, dried over MgSO4 filtered and evaporated. The residue was purified on preparative RP HPLC (acetonitrile/water) and on silica gel (EtOAc/hexanes) and the product was co-evaporated with ethanol to give 2-(3-hydroxy-4-(4-methylthiophen-3-yl)phenyl)-N-isobutyl-2-methylpropanamide (69 mg, 70%). 1H NMR (400 MHz, dMSO): δ 0.74-0.76 (d, 6H), 1.42 (s, 6H), 1.67-1.74 (m, 1H), 2.09 (s, 3H), 2.83-2.86 (t, 2H), 6.76-6.78 (dd, 1H), 6.87-6.88 (d, 1H), 7.01-7.03 (d, 1H), 7.13-7.14 (m, 1H), 7.21-7.22 (d, 1H), 7.27-7.29 (t, 1H), 9.38-9.39 (b, 1H); MS (332).

Workup

washThe organic phase was washed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customThe residue was purified on preparative RP HPLC (acetonitrile/water) and on silica gel (EtOAc/hexanes)

Sources & evidence

ORD record: ord-5d0475755f444f158e16865bc062fbe4
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842324B2

Reaction notes

Loading…