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

HRID 531693Notes

Reaction equation

HRID 531693 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:39]=[C:40]([F:42])[CH:41]=1)[CH2:5][N:6]1[CH:10]=[CH:9][C:8]([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)=[CH:22][CH:21]=4)[CH:18]=3)[NH:13][CH:12]=2)=[N:7]1.CO.[ClH:45]>C(OCC)C>[ClH:45].[F:1][C:2]1[CH:3]=[C:4]([CH:39]=[C:40]([F:42])[CH:41]=1)[CH2:5][N:6]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:21]=[CH:22][C:23]([N:26]5[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]5)=[CH:24][CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)=[N:7]1

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 136492678tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate

Product 1

HCID 1369602763-(1-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-5-(4-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine hydrochlorideYield 62.5%

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-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (27 mg, 0.047 mmol) was deprotected in methanol/HCl in diethyl ether (2/1 ml) to afford 15 mg (62.5% yield) of the titled compound. 1H NMR (DMSO-d6, 300 MHz): δ 11.9 (s, 1H), 9.10-9.00 (bs, 2H), 8.598-8.52 (m, 2H), 7.91-7.89 (m, 2H), 7.60-7.57 (d, 2H), 7.17-7.00 (m, 4H), 6.71-6.70 (d, 1H), 5.41 (s, 2H), 3.23 (s, 5H). MS: m/z=471.3 (M+1), HPLC: 97.74% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-f05cbb4791a94e77b55078e12848938c
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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