Hydrochloric Acid → HCID 86633144, compound

HRID 1926266Notes

Reaction equation

HRID 1926266 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[N:21][C:22]([NH2:38])=[C:23]([C:25]4[N:26]=[CH:27][C:28]5[C:33]([CH:34]=4)=[C:32]([Cl:35])[C:31]([F:36])=[CH:30][C:29]=5[F:37])[CH:24]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:39]>C(Cl)Cl.CCOCC>[ClH:35].[ClH:39].[ClH:35].[Cl:35][C:32]1[C:31]([F:36])=[CH:30][C:29]([F:37])=[C:28]2[C:33]=1[CH:34]=[C:25]([C:23]1[C:22]([NH2:38])=[N:21][CH:20]=[C:19]([C:17]3[CH:16]=[N:15][N:14]([CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[CH:18]=3)[CH:24]=1)[N:26]=[CH:27]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67520633HCID 67520633, compound

Product 1

HCID 86633144HCID 86633144, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

4-{4-[6-Amino-5-(5-chloro-6,8-difluoroisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (0.0311 mmol) was dissolved in DCM (4.4 ml), and 1.0 M of HCl in Et2O (8.8 ml) was added. The mixture was stirred at rt for 16 h. After that time, solvent was removed in vacuo to give the title compound as a yellow powder. 1H NMR (400 MHz, DMSO-d6): δ=2.14-2.30 (m, 4H), 3.03-3.18 (m, 2H), 3.36-3.42 (m, 2H), 4.50-4.60 (m, 1H), 4.97 (brs, 2H), 8.07 (t, J=10.0 Hz, 1H), 8.14 (s, 1H), 8.49 (s, 1H), 8.53 (d, J=2.4 Hz, 1H), 8.63 (d, J=0.8 Hz, 1H), 8.81 (d, J=2.4 Hz, 1H), 9.14 (brs, 1H), 9.31 (brs, 1H), 9.66 (s, 1H). MS(ES+): m/z=440.84/442.79 (82/32) [MH+]. HPLC: tR=1.89 min (ZQ3, polar—5 min).

Workup

  1. customAfter that time, solvent was removed in vacuo

Sources & evidence

ORD record
ord-99d572d0d62c4d5cb3fb02f814d3d7df
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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