Dimethyl Sulfoxide → HCID 178472675, compound

HRID 1401199Notes

Reaction equation

Br[C:2]1[C:3]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[CH3:16][O:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20][CH2:19]1.C(N(CC)C(C)C)(C)C.CS(C)=O>C(OCC)(=O)C>[Br:8][C:6]1[N:7]=[C:2]([NH:24][C@H:21]2[CH2:22][CH2:23][C@H:18]([O:17][CH3:16])[CH2:19][CH2:20]2)[C:3]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:4][CH:5]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetate (See Example 6.B) (30.0 g, 88 mmol), trans-4-methoxycyclohexanamine (17.15 g, 133 mmol), N,N-diisopropylethylamine (30.8 mL, 177 mmol) and dimethylsulfoxide (70.8 mL) were combined in a reaction vial with a stirbar and heated in an oil bath at 150° C. for 16 h with stirring. The resulting mixture was diluted with ethyl acetate and the volatiles removed under reduced pressure. The residue was purified using silica gel chromatography on a Biotage SP1 (12% ethyl acetate in hexanes). Fractions containing the desired product were combined and organic volatiles removed under reduced pressure. The residue was triturated with 5% ethyl acetate in hexane. Solids were collected by vacuum filtration, washed with hexane and dried under vacuum to afford ethyl the title compound (15.37 g, 39.7 mmol, 44.8% yield) as an off-white solid. MS (ESI) m/z 387.0 [M]+, 389.0 [M+2]+.

Workup

customthe volatiles removed under reduced pressure
customThe residue was purified
additionFractions containing the desired product
customorganic volatiles removed under reduced pressure
customThe residue was triturated with 5% ethyl acetate in hexane
filtrationSolids were collected by vacuum filtration
washwashed with hexane
customdried under vacuum

Sources & evidence

ORD record: ord-7197bce3e6e644a2a1636c23efc63c87
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907087B2

Reaction notes

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