Hydrochloric Acid → HCID 67520429, compound

HRID 1926279Notes

Reaction equation

HRID 1926279 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH:19]=[C:18]([C:20]3[CH:21]=[N:22][C:23]([NH2:37])=[C:24]([C:26]4[N:27]=[CH:28][C:29]5[C:34]([CH:35]=4)=[CH:33][CH:32]=[C:31]([F:36])[CH:30]=5)[CH:25]=3)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)=O)(C)(C)C>C(OCC)C.C(Cl)Cl>[F:36][C:31]1[CH:30]=[C:29]2[C:34]([CH:35]=[C:26]([C:24]3[C:23]([NH2:37])=[N:22][CH:21]=[C:20]([C:18]4[CH:17]=[N:16][N:15]([CH:12]5[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]5)[CH:19]=4)[CH:25]=3)[N:27]=[CH:28]2)=[CH:33][CH:32]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67521103HCID 67521103, compound

Product 1

HCID 67520429HCID 67520429, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

For the deprotection, 1N HCl in diethyl ether (1.0 mL) was added to a solution of 4-{4-[6-amino-5-(7-fluoroisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (entire quantity isolated in the previous step) in DCM (1.0 mL) in a sealed test tube. The reaction stirred at rt for 1 h. The mixture was concentrated in vacuo to give the title compound as yellow solid. 1H NMR (400 MHz, CD3OD): δ=2.37 (4H, br.s), 3.54-3.68 (3H, m), 4.20 (1H, d, J=5.6 Hz), 4.64 (1H, br.s), 7.58-7.72 (1H, m), 7.81 (1H, br.s), 7.98 (1H, br.s), 8.06 (1H, br.s), 8.27 (2H, br.s), 8.69-8.90 (2H, m), 9.48 (1H, br.s). HPLC: tR=1.74 min. (ZQ2, polar—5 min.). MS (ES+): m/z=389.18 (95) [MH+].

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-7f85e5c0e7fc404ab320c993f4d76cca
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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