5-chloro-1-isopropyl-4-nitro-1H-pyrazole → (R)-2,2,2-trifluoro-N-(1-(1-isopropyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl)acetamide

HRID 2089420Notes

Reaction equation

HRID 2089420 reaction equation
Cl[C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[NH:13]1[CH2:19][CH2:18][CH2:17][C@@H:16]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH2:15][CH2:14]1>>[F:25][C:22]([F:23])([F:24])[C:21]([NH:20][C@@H:16]1[CH2:17][CH2:18][CH2:19][N:13]([C:2]2[N:6]([CH:7]([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH2:14][CH2:15]1)=[O:26]

Participants

3

Reactant 2

HCID 584648025-chloro-1-isopropyl-4-nitro-1H-pyrazoleHCID 86658411(R)-N-(azepan-4-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 86658425(R)-2,2,2-trifluoro-N-(1-(1-isopropyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl)acetamideYield 52%

Procedure

Reaction of 5-chloro-1-isopropyl-4-nitro-1H-pyrazole and (R)-N-(azepan-4-yl)-2,2,2-trifluoroacetamide gave (R)-2,2,2-trifluoro-N-(1-(1-isopropyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl)acetamide as a pale yellow gum (90 mg, 52%). 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 6.39 (s, 1H), 4.83-4.70 (m, 1H), 4.24-4.17 (m, 1H), 3.45-3.32 (m, 1H), 3.28-3.12 (m, 3H), 2.23-2.02 (m, 2H), 2.00-1.80 (m, 4H), 1.54-1.44 (m, 6H)

Sources & evidence

ORD record
ord-72e9ccd46173483298e55402d9ea2c8b
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

Loading…