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

HRID 2089313Notes

Reaction equation

HRID 2089313 reaction equation
Cl[C:2]1[N:6]([CH2:7][CH:8]2[CH2:10][CH2:9]2)[N:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[F:14][C:15]([F:27])([F:26])[C:16]([NH:18][C@@H:19]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:17]>>[CH:8]1([CH2:7][N:6]2[C:2]([N:22]3[CH2:23][CH2:24][CH2:25][C@@H:19]([NH:18][C:16](=[O:17])[C:15]([F:26])([F:14])[F:27])[CH2:20][CH2:21]3)=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=[N:5]2)[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 584648135-Chloro-1-(cyclopropylmethyl)-4-nitro-1h-pyrazoleHCID 86658411(R)-N-(azepan-4-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 86658414(R)-N-(1-(1-cyclopropylmethyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl)-2,2,2-trifluoroacetamideYield 55%

Procedure

Following the procedure for Example 503 starting with 5-chloro-1-cyclopropylmethyl-4-nitro-1H-pyrazole and (R)-2,2,2-trifluoro-N-(hexahydro-1H-azepin-4-yl)-acetamide gave (R)-N-(1-(1-cyclopropylmethyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl)-2,2,2-trifluoroacetamide as a pale yellow gum (0.98 g, 55%). 1H-NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 6.42-6.39 (m, 1H), 4.22-4.14 (m, 1H), 4.00-3.85 (m, 2H), 3.44-3.32 (m, 1H), 3.30-3.15 (m, 3H), 2.25-2.05 (m, 2H), 2.00-1.75 (m, 4H), 1.30-1.20 (m, 1H), 0.70-0.62 (m, 2H), 0.50-0.35 (m, 2H).

Sources & evidence

ORD record
ord-29bc7de92fd744a8ada68e98437325c6
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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