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

HRID 531683Notes

Reaction equation

HRID 531683 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][C:35]6[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=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].[F:41][C:37]1[CH:36]=[C:35]([CH:40]=[CH:39][CH:38]=1)[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

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 90034218tert-butyl 5-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-3-(methylsulfonamido)phenyl)-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 90030962N-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)phenyl)methanesulfonamide hydrochlorideYield 57%

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-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (27 mg, mmol) was deprotected in methanol/HCl in diethyl ether (3/1 ml) to afford 12 mg (57% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 9.01-9.00 (d, 1H), 8.71-8.70 (d, 1H), 8.41 (s, 1H), 8.09 (s, 1H), 7.98 (s, 1H), 7.87-7.86 (d, 1H), 7.66-7.63 (dd, 1H), 7.49-7.46 (d, 1H), 7.40-7.34 (m, 1H), 7.16-7.13 (m, 1H), 7.07-7.02 (m, 2H), 5.47 (s, 2H), 3.50-3.46 (m, 4H), 3.26-3.23 (m, 7H). MS: m/z=546.2 (M+1), HPLC: 98.49% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-a06ae2052b134ef983065655cc59d64e
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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