Hydrochloric Acid → 6-cyclopropyl-3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(4-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine hydrochloride

HRID 531575Notes

Reaction equation

HRID 531575 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:31]([C:32]5[C:33]([CH3:47])=[N:34][N:35]([CH2:38][C:39]6[CH:44]=[C:43]([F:45])[CH:42]=[C:41]([F:46])[CH:40]=6)[C:36]=5[CH3:37])=[CH:30][N:29](C(OC(C)(C)C)=O)[C:23]4=[N:24][C:25]=3[CH:26]3[CH2:28][CH2:27]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:55]>CO>[ClH:55].[CH:26]1([C:25]2[N:24]=[C:23]3[NH:29][CH:30]=[C:31]([C:32]4[C:33]([CH3:47])=[N:34][N:35]([CH2:38][C:39]5[CH:44]=[C:43]([F:45])[CH:42]=[C:41]([F:46])[CH:40]=5)[C:36]=4[CH3:37])[C:22]3=[CH:21][C:20]=2[C:17]2[CH:18]=[CH:19][C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:15][CH:16]=2)[CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90030898tert-butyl 5-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-6-cyclopropyl-3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 1185240316-cyclopropyl-3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(4-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine hydrochlorideYield 5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using similar reaction conditions as described in Step-ii of example-7, tert-butyl 5-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-6-cyclopropyl-3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (62 mg, 0.022 mmol) was deprotected in HCl in methanol (2 ml). This afforded 4 mg (5% yield) of the titled compound. 1H NMR (CDCl3, 300 MHz): δ 8.44 (b, 1H), 7.68 (s, 1H), 7.42-7.39 (d, 2H), 7.02-7.00 (d, 2H), 6.661-6.641 (m, 1H), 6.311-6.305 (d, 1H), 5.26 (s, 2H), 3.25-3.21 (m, 3H), 3.10-3.07 (t, 3H), 2.41 (s, 3H), 2.32 (s, 3H), 1.13-1.10 (m, 2H), 0.88-0.85 (m, 4H). MS: m/z=539.2 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-e808677eb1e84c54b1bf975d7b102a6e
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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