tert-butyl 4-(5-(3-(1-benzyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazine-1-carboxylate → 3-(1-benzyl-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 531792Notes

Reaction equation

HRID 531792 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:22]4[CH:23]=[CH:24][C:25]([N:28]5[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]5)=[N:26][CH:27]=4)[CH:20]=3)[N:15]([S:41]([C:44]3[CH:50]=[CH:49][C:47]([CH3:48])=[CH:46][CH:45]=3)(=[O:43])=[O:42])[CH:14]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl.CCOCC>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:22]4[CH:27]=[N:26][C:25]([N:28]5[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]5)=[CH:24][CH:23]=4)[CH:20]=3)[N:15]([S:41]([C:44]3[CH:45]=[CH:46][C:47]([CH3:48])=[CH:49][CH:50]=3)(=[O:42])=[O:43])[CH:14]=2)[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 118524035tert-butyl 4-(5-(3-(1-benzyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 1185241083-(1-benzyl-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineYield 70.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(5-(3-(1-benzyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazine-1-carboxylate (100 mg, 0.144 mmol) was deprotected in HCl in ether (8 ml) to afford 60 mg (66.1% yield) of the titled compound.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-8e1d29214ba744c3ac6b5576bddfe9f0
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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