Diisopropylethylamine → HCID 58009935, compound

HRID 1854385Notes

Reaction equation

Cl.[S:2]([N:12]1[C:16]2=[N:17][CH:18]=[C:19]([NH2:21])[N:20]=[C:15]2[CH:14]=[CH:13]1)([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[CH2:23][C:24]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=O.CCN(C(C)C)C(C)C>CCCCO>[CH:26]1([C:24]2[N:21]=[C:19]3[CH:18]=[N:17][C:16]4[N:12]([S:2]([C:5]5[CH:6]=[CH:7][C:8]([CH3:9])=[CH:10][CH:11]=5)(=[O:3])=[O:4])[CH:13]=[CH:14][C:15]=4[N:20]3[CH:23]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

Conditions

Temperature: 170 °C

Procedure

To a suspension of 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-amine hydrochloride (0.10 g, 0.35 mmol) and 2-bromo-1-cyclohexylethanone (0.078 g, 0.38 mmol, 3B Pharmachem) in n-BuOH (1.5 mL) was added DIEA (0.067 g, 0.52 mmol) and the resulting solution was heated at about 170° C. in the CEM™ microwave for about 30 min. The solvent was removed under reduced pressure to afford 7-cyclohexyl-3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine as a crude solid that was used in Step D without further purification: LC/MS (Table 2, Method a) Rt=2.71 min; MS m/z: 395 (M+H)+.

Workup

customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-6defbf2ca41d4cc68cef7598798f5084
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962629B2

Reaction notes

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