5-Chloro-1-cyclopropyl-4-nitro-1H-pyrazole → (R)-N-(1-(1-cyclopropyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl)-2,2,2-trifluoroacetamide

HRID 1915739Notes

Reaction equation

HRID 1915739 reaction equation
Cl[C:2]1[N:6]([CH:7]2[CH2:9][CH2:8]2)[N:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[F:13][C:14]([F:26])([F:25])[C:15]([NH:17][C@@H:18]1[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:16]>>[CH:7]1([N:6]2[C:2]([N:21]3[CH2:22][CH2:23][CH2:24][C@@H:18]([NH:17][C:15](=[O:16])[C:14]([F:25])([F:13])[F:26])[CH2:19][CH2:20]3)=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=[N:5]2)[CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 584647665-Chloro-1-cyclopropyl-4-nitro-1H-pyrazoleHCID 86658411(R)-N-(azepan-4-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 86658415(R)-N-(1-(1-cyclopropyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl)-2,2,2-trifluoroacetamideYield 61%

Procedure

Following the procedure for Example 503 starting with 5-chloro-1-cyclopropyl-4-nitro-1H-pyrazole and (R)-2,2,2-trifluoro-N-(hexahydro-1H-azepin-4-yl)-acetamide gave (R)—N-(1-(1-cyclopropyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl)-2,2,2-trifluoroacetamide as a pale yellow gum (0.105 g, 61%). 1H-NMR (400 MHz, CDCl3) δ 7.96 (s, 1H), 6.55-6.38 (m, 1H), 4.30-4.15 (m, 1H), 3.65-3.53 (m, 1H), 3.55-3.25 (m, 4H), 2.25-2.05 (m, 6H), 1.35-1.05 (m, 4H).

Sources & evidence

ORD record
ord-326e795235db421f88fd26e5316439fb
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

Loading…