Tert-butyl 4-azido-5-hydroxyazepane-1-carboxylate → 5-azido-1-(1-(2,2-difluoroethyl)-4-nitro-1H-pyrazol-5-yl)azepan-4-ol

HRID 1915790Notes

Reaction equation

HRID 1915790 reaction equation
FC1C(=O)CCN(C2NN=CC=2[N+]([O-])=O)C1.[N:17]([CH:20]1[CH:26]([OH:27])[CH2:25][CH2:24][N:23]([C:28](OC(C)(C)C)=O)[CH2:22][CH2:21]1)=[N+:18]=[N-:19].ClC1[N:40]([CH2:41][CH:42]([F:44])[F:43])[N:39]=[CH:38][C:37]=1[N+:45]([O-:47])=[O:46]>>[N:17]([CH:20]1[CH2:21][CH2:22][N:23]([C:28]2[N:40]([CH2:41][CH:42]([F:44])[F:43])[N:39]=[CH:38][C:37]=2[N+:45]([O-:47])=[O:46])[CH2:24][CH2:25][CH:26]1[OH:27])=[N+:18]=[N-:19]

Participants

4

Reactant 3

HCID 58717042Tert-butyl 4-azido-5-hydroxyazepane-1-carboxylateHCID 866799533-fluoro-1-(4-nitro-1H-pyrazol-5-yl)piperidin-4-oneHCID 86679965HCID 86679965, compound

Product 1

HCID 866800025-azido-1-(1-(2,2-difluoroethyl)-4-nitro-1H-pyrazol-5-yl)azepan-4-ol

Procedure

Following the procedure for Intermediate 48 starting from tert-butyl 4-azido-5-hydroxyazepane-1-carboxylate and 5-chloro-1-(2,2-difluoroethyl)-4-nitro-1H-pyrazole gave 5-azido-1-(1-(2,2-difluoroethyl)-4-nitro-1H-pyrazol-5-yl)azepan-4-ol as a yellow gum (1.16 g, 50% over two steps). 1H NMR (400 MHz, CDCl3) δ 8.14-8.09 (m, 1H), 6.11 (tt, J=27.8, 4.4 Hz, 1H), 4.50-4.39 (m, 2H), 3.83 (tt, J=8.8, 3.1 Hz, 1H), 3.67 (td, J=4.7, 3.6 Hz, 1H), 3.45-3.21 (m, 4H), 2.37 (d, J=2.9 Hz, 1H), 2.25-2.12 (m, 2H), 2.03-1.91 (m, 2H).

Sources & evidence

ORD record
ord-852ee2aedb0142eea1571d74a5187d12
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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