5-bromo-4-nitro-1-(2,2,2-trifluoroethyl)-1H-pyrazole → (R)-N-(1-(4-amino-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl)azepan-4-yl)-2,2,2-trifluoroacetamide

HRID 1915780Notes

Reaction equation

HRID 1915780 reaction equation
Br[C:2]1[N:6]([CH2:7][C:8]([F:11])([F:10])[F:9])[N:5]=[CH:4][C:3]=1[N+:12]([O-])=O.[NH:15]1[CH2:21][CH2:20][CH2:19][C@@H:18]([NH:22][C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[CH2:17][CH2:16]1>>[NH2:12][C:3]1[CH:4]=[N:5][N:6]([CH2:7][C:8]([F:11])([F:10])[F:9])[C:2]=1[N:15]1[CH2:21][CH2:20][CH2:19][C@@H:18]([NH:22][C:23](=[O:28])[C:24]([F:26])([F:25])[F:27])[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 569733215-bromo-4-nitro-1-(2,2,2-trifluoroethyl)-1H-pyrazoleHCID 86658411(R)-N-(azepan-4-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 86679992(R)-N-(1-(4-amino-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl)azepan-4-yl)-2,2,2-trifluoroacetamideYield 53.6%

Procedure

Following the procedure for Intermediate 8 starting from 5-bromo-4-nitro-1-(2,2,2-trifluoroethyl)-1H-pyrazole (150 mg, 0.55 mmol) and (R)—N-(azepan-4-yl)-2,2,2-trifluoroacetamide (115 mg, 0.55 mmol) gave (R)—N-(1-(4-amino-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl)azepan-4-yl)-2,2,2-trifluoroacetamide as a colourless gum (110 mg, 53%). 1H NMR (400 MHz, CDCl3) δ 7.25 (s, 1H), 7.11 (br s, 1H), 4.54 (q, J=8.5 Hz, 2H), 4.35-4.22 (m, 1H), 3.40-3.23 (m, 2H), 3.21-3.08 (m, 2H), 2.62 (br s, 2H), 2.17-2.08 (m, 1H), 2.06-1.91 (m, 1H), 1.92-1.71 (m, 4H).

Sources & evidence

ORD record
ord-fe5c1687e1774afa8e4896713416f85b
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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