Diisopropylethylamine → HCID 86680072, compound

HRID 1915861Notes

Reaction equation

[F:1][CH:2]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4][CH:3]1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].CCN(C(C)C)C(C)C.Cl[C:27]1[N:31]([CH3:32])[N:30]=[CH:29][C:28]=1[N+:33]([O-:35])=[O:34]>CCO>[F:1][CH:2]1[CH2:8][CH2:7][N:6]([C:27]2[N:31]([CH3:32])[N:30]=[CH:29][C:28]=2[N+:33]([O-:35])=[O:34])[CH2:5][CH2:4][CH:3]1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of tert-butyl 5-fluoroazepan-4-ylcarbamate (310 mg, 1.34 mmol) in EtOH (4 mL) was added DIPEA (1 ml, 5.7 mmol) and 5-chloro-1-methyl-4-nitro-1H-pyrazole (216 mg, 1.34 mmol). The reaction mixture was heated at 130° C. in a microwave for 8 hr. The solvent was removed under reduced pressure and the residue was purified via silica gel column chromatography (30-40% EtOAc/isohexane) to give the two trans (anti) isomers, tert-butyl 5-fluoro-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepan-4-ylcarbamate as a yellow glass (65 mg) contaminated with some of the cis (syn) isomer.

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified via silica gel column chromatography (30-40% EtOAc/isohexane)

Sources & evidence

ORD record: ord-b74aad6aa60b4d1ab63b2789182250db
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614206B2

Reaction notes

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