Sodium Dithionite → (S)-6-(2-benzyl-4-(1-cyclobutyl-3-ethyl-1H-indazol-6-yl)piperazin-1-yl)pyridin-2-amine

HRID 1423246Notes

Reaction equation

HRID 1423246 reaction equation
[CH2:1]([CH:8]1[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[N:15]=2)[CH2:12][CH2:11][N:10]([C:23]2[CH:31]=[C:30]3[C:26]([C:27]([CH2:36][CH3:37])=[N:28][N:29]3[CH:32]3[CH2:35][CH2:34][CH2:33]3)=[CH:25][CH:24]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1COCC1.O>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:23]2[CH:31]=[C:30]3[C:26]([C:27]([CH2:36][CH3:37])=[N:28][N:29]3[CH:32]3[CH2:35][CH2:34][CH2:33]3)=[CH:25][CH:24]=2)[CH2:11][CH2:12][N:13]1[C:14]1[N:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 668262786-[3-benzyl-4-(6-nitro-pyridin-2-yl)-piperazin-1-yl]-1-cyclobutyl-3-ethyl-1H-indazole

Product 1

HCID 52920015(S)-6-(2-benzyl-4-(1-cyclobutyl-3-ethyl-1H-indazol-6-yl)piperazin-1-yl)pyridin-2-amineYield 2%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Prepared using the same procedure described in Example 410 from 6-(3-benzyl-piperazin-1-yl)-1-cyclobutyl-3-ethyl-1H-indazole and 2-chloro-6-nitro-pyridine to afford the intermediate 6-[3-benzyl-4-(6-nitro-pyridin-2-yl)-piperazin-1-yl]-1-cyclobutyl-3-ethyl-1H-indazole {20.5 mg; LC/MS (Method B) 5.09 min, [M+1]+ 497]}. The nitro-intermediate was reduced with sodium hydrosulfite (48 mg, 0.28 mmol) in 50:50 THF/water at room temperature to obtain the title compound as a tan solid (6 mg, 2% overall). LC/MS (Method B) 4.02 min, [M+1]+ 467.

Workup

  1. customLC/MS (Method B) 5.09 min, [M+1]+ 497

Sources & evidence

ORD record
ord-a3216a60260d4a12a41cd950f4e7580a
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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