Hydrochloride methanol → 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(3-methoxy-4-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride

HRID 531695Notes

Reaction equation

HRID 531695 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:51]=[CH:52][CH:53]=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:25]=[CH:24][C:23]([N:26]5[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]5)=[C:22]([O:39][CH3:40])[CH:21]=4)[CH:18]=3)[N:13]([S:41]([C:44]3[CH:50]=[CH:49][C:47]([CH3:48])=[CH:46][CH:45]=3)(=[O:43])=[O:42])[CH:12]=2)[CH:8]=[N:7]1.CO.[ClH:56]>C(OCC)C>[ClH:56].[F:1][C:2]1[CH:3]=[C:4]([CH:51]=[CH:52][CH:53]=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:25]=[CH:24][C:23]([N:26]5[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]5)=[C:22]([O:39][CH3:40])[CH:21]=4)[CH:18]=3)[N:13]([S:41]([C:44]3[CH:45]=[CH:46][C:47]([CH3:48])=[CH:49][CH:50]=3)(=[O:42])=[O:43])[CH:12]=2)[CH:8]=[N:7]1

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 90031268tert-butyl 4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)piperazine-1-carboxylate

Product 1

HCID 900313783-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(3-methoxy-4-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochlorideYield 69%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)piperazine-1-carboxylate (190 mg, 0.257 mmol) was deprotected in methanol/HCl in diethyl ether (5/3 ml) to afford 120 mg (69.0% yield) of the titled compound. MS: m/z=637.3 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-d8fc458be326489a8e5200a3d137a806
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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