Tert-butyl 1,4-diazepane-1-carboxylate → tert-butyl 4-(4-nitro-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl)-1,4-diazepane-1-carboxylate

HRID 1915781Notes

Reaction equation

HRID 1915781 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-:14])=[O:13].[N:15]1([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>>[N+:12]([C:3]1[CH:4]=[N:5][N:6]([CH2:7][C:8]([F:11])([F:10])[F:9])[C:2]=1[N:18]1[CH2:19][CH2:20][CH2:21][N:15]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:16][CH2:17]1)([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 569733215-bromo-4-nitro-1-(2,2,2-trifluoroethyl)-1H-pyrazole

Product 1

HCID 86679993tert-butyl 4-(4-nitro-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl)-1,4-diazepane-1-carboxylateYield 91%

Procedure

Following the procedure for Intermediate 22 starting from 5-bromo-4-nitro-1-(2,2,2-trifluoroethyl)-1H-pyrazole and tert-butyl 1,4-diazepane-1-carboxylate gave tert-butyl 4-(4-nitro-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl)-1,4-diazepane-1-carboxylate as a pale yellow gum (197 mg, 91%). 1H NMR (400 MHz, CDCl3) δ 8.19-8.12 (m, 1H), 4.76-4.66 (m, 2H), 3.65-3.49 (m, 4H), 3.32-3.23 (m, 4H), 1.92-1.78 (m, 2H), 1.52-1.47 (m, 9H).

Sources & evidence

ORD record
ord-c6fd60db6aff4842888dd4616f5a1d65
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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