1,1-Dimethylethyl (2S)-2-(phenylmethyl)-1-piperazinecarboxylate → (S)-5-(3-benzylpiperazin-1-yl)-3-cyclobutyl-1-isopropyl-1H-indazole

HRID 1423109Notes

Reaction equation

HRID 1423109 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]([CH3:13])[CH3:12])[N:6]=[C:5]2[CH:14]1[CH2:17][CH2:16][CH2:15]1.C(OC([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][C@@H:26]1[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=O)(C)(C)C>>[CH2:31]([C@@H:26]1[NH:25][CH2:30][CH2:29][N:28]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([CH:11]([CH3:13])[CH3:12])[N:6]=[C:5]3[CH:14]2[CH2:17][CH2:16][CH2:15]2)[CH2:27]1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 177504411,1-Dimethylethyl (2S)-2-(phenylmethyl)-1-piperazinecarboxylateHCID 581890485-Bromo-3-cyclobutyl-1-isopropyl-1H-indazole

Product 1

HCID 58189257(S)-5-(3-benzylpiperazin-1-yl)-3-cyclobutyl-1-isopropyl-1H-indazoleYield 55%

Procedure

The title compound was prepared by the method outlined for Example 1 using 5-Bromo-3-cyclobutyl-1-isopropyl-1H-indazole as the aryl halide and (S)-2-benzyl-piperazine-1-carboxylic acid tert-butyl ester as the amine component to afford the title compound as a brown oil (780 mg, 55%). 1H NMR (MeOH-d4) 7.44-7.20 (m, 5H), 7.16-6.87 (m, 3H), 4.78 (td, J=13.4, 6.7 Hz, 1H), 3.95-3.83 (m, 1H), 3.46-3.33 (m, 2H), 3.20-3.05 (m, 2H), 3.03-2.91 (m, 1H), 2.82-2.75 (m, 3H), 2.57-2.36 (m, 6H), 2.24-2.09 (m, 1H), 1.50 (d, J=6.7 Hz, 6H). LC/MS (Method B) 2.79 min, [M+1]+ 389.

Workup

  1. customThe title compound was prepared by the method

Sources & evidence

ORD record
ord-5421b20db99641b1ab0353517412e514
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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