tert-butyl 4-(3-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)benzyl)piperidine-1-carboxylate → 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(3-(piperidin-4-ylmethyl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride

HRID 531883Notes

Reaction equation

HRID 531883 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:50]=[CH:51][CH:52]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:21]=[C:22]([CH:37]=[CH:38][CH:39]=4)[CH2:23][CH:24]4[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]4)[CH:18]=3)[N:13]([S:40]([C:43]3[CH:49]=[CH:48][C:46]([CH3:47])=[CH:45][CH:44]=3)(=[O:42])=[O:41])[CH:12]=2)[CH:8]=[N:7]1.CO.CCOCC.[ClH:60]>>[ClH:60].[F:1][C:2]1[CH:3]=[C:4]([CH:50]=[CH:51][CH:52]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:39]=[CH:38][CH:37]=[C:22]([CH2:23][CH:24]5[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]5)[CH:21]=4)[CH:18]=3)[N:13]([S:40]([C:43]3[CH:44]=[CH:45][C:46]([CH3:47])=[CH:48][CH:49]=3)(=[O:41])=[O:42])[CH:12]=2)[CH:8]=[N:7]1

Participants

3

Reactant 2

HCID 90031256tert-butyl 4-(3-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)benzyl)piperidine-1-carboxylateHCID 131735674methanol ether HCl

Product 1

HCID 900306093-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(3-(piperidin-4-ylmethyl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochlorideYield 72.4%

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(3-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)benzyl)piperidine-1-carboxylate (compound of step 1 of example 102) (32 mg, 0.44 mmol) was deprotected in methanol/ether HCl (5/0.3 ml). This afforded 210 mg (72.4% yield) of the titled compound.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-6e3fc53f00d6433b9142120f6517fa37
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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