Diisopropylethylamine → HCID 178491295, compound

HRID 518674Notes

Reaction equation

F[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].Cl.[NH2:22][C@@H:23]1[CH2:28][CH2:27][C@H:26]([C:29]([NH:31][CH:32]([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1.CCN(C(C)C)C(C)C>C(#N)C>[CH:32]([NH:31][C:29]([C@H:26]1[CH2:25][CH2:24][C@@H:23]([NH:22][C:2]2[CH:7]=[C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)[CH:5]=[CH:4][C:3]=2[N+:18]([O-:20])=[O:19])[CH2:28][CH2:27]1)=[O:30])([CH3:34])[CH3:33]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-fluoro-4-(4-methoxybenzyloxy)-1-nitrobenzene (507 mg, 1.82 mmol), cis-4-amino-N-isopropylcyclohexanecarboxamide hydrochloride (404 mg, 1.82 mmol), DIPEA (0.70 mL, 4.02 mmol) and ACN (3.6 mL) were placed in a sealed tube, and the tube was heated at 80° C. for 6 hours. The mixture was allowed to cool and evaporated. The residue was diluted with DCM (15 mL), washed with water (×2), and then washed with brine. The organic layer was dried over Na2SO4. The mixture was purified via flash chromatography using a linear gradient of 0% to 10% MeOH in DCM. The title compound was collected as a yellow solid (476 mg, 59% yield).

Workup

customwere placed in a sealed tube
temperatureto cool
customevaporated
additionThe residue was diluted with DCM (15 mL)
washwashed with water (×2)
washwashed with brine
dry with materialThe organic layer was dried over Na2SO4
customThe mixture was purified via flash chromatography

Sources & evidence

ORD record: ord-531055dfb41a4dc4b631601f300a762e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115127B2

Reaction notes

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