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

HRID 1423108Notes

Reaction equation

HRID 1423108 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[N:6]=[C:5]2[CH:12]1[CH2:15][CH2:14][CH2:13]1.C(OC([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][C@@H:24]1[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=O)(C)(C)C>>[CH2:29]([C@@H:24]1[NH:23][CH2:28][CH2:27][N:26]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([CH3:11])[N:6]=[C:5]3[CH:12]2[CH2:15][CH2:14][CH2:13]2)[CH2:25]1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

3

Reactant 2

HCID 177504411,1-Dimethylethyl (2S)-2-(phenylmethyl)-1-piperazinecarboxylateHCID 581889995-Bromo-3-cyclobutyl-1-methyl-1H-indazole

Product 1

HCID 58189168(S)-5-(3-benzylpiperazin-1-yl)-3-cyclobutyl-1-methyl-1H-indazoleYield 99%

Procedure

The title compound was prepared by the method outlined for Example 1 using 5-Bromo-3-cyclobutyl-1-methyl-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 (409 mg, 99%). 1H NMR (MeOH-d4) 8.72 (d, J=8.7 Hz, 1H), 7.79 (d, J=8.8 Hz, 1H), 7.32-7.18 (m, 6H), 4.08 (s, 3H), 3.79-3.46 (m, 3H), 3.35-3.34 (m, 1H), 3.31-3.30 (m, 2H), 3.15-3.07 (m, 4H), 2.88-2.77 (m, 5H), 2.69-2.61 (m, 1H). LC/MS (Method B) 2.49 min, [M+1]+ 361.

Workup

  1. customThe title compound was prepared by the method

Sources & evidence

ORD record
ord-e16e87e0e4524d32aaaa33b8d404daa4
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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