Hydrochloride methanol → N-(5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)phenyl)methanesulfonamide hydrochloride

HRID 531685Notes

Reaction equation

HRID 531685 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[C:22]4[C:28]([C:29]5[CH:30]=[N:31][N:32]([CH2:34][CH2:35][C:36]6[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=6)[CH:33]=5)=[CH:27][N:26](C(OC(C)(C)C)=O)[C:23]4=[N:24][CH:25]=3)=[CH:16][C:15]=2[NH:49][S:50]([CH3:53])(=[O:52])=[O:51])[CH2:10][CH2:9]1)=O)(C)(C)C.CO.[ClH:56]>C(OCC)C>[ClH:56].[CH2:34]([N:32]1[CH:33]=[C:29]([C:28]2[C:22]3[C:23](=[N:24][CH:25]=[C:20]([C:17]4[CH:18]=[CH:19][C:14]([N:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[C:15]([NH:49][S:50]([CH3:53])(=[O:52])=[O:51])[CH:16]=4)[CH:21]=3)[NH:26][CH:27]=2)[CH:30]=[N:31]1)[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 90030733tert-butyl 5-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-3-(methylsulfonamido)phenyl)-3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 72944426N-(5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)phenyl)methanesulfonamide hydrochlorideYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 5-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-3-(methylsulfonamido)phenyl)-3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (21 mg, mmol) was deprotected in methanol/HCl in diethyl ether (2/1 ml) to afford 11 mg (68% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.859-8.853 (d, 1H), 8.736-8.73 (d, 1H), 8.37 (s, 1H), 8.33 (s, 1H), 8.00 (s, 1H), 7.867-7.861 (d, 1H), 7.66-7.63 (dd, 1H), 7.53-7.50 (d, 1H), 7.27-7.12 (m, 5H), 4.63-4.61 (t, 2H), 3.51-3.47 (t, 4H), 3.50-3.24 (m, 9H). MS: m/z=542.3 (M+1), HPLC: 98.49% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-feb6c034606248d6a23867d2db407392
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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