Hydrochloric Acid → HCID 67521041, compound

HRID 1926445Notes

Reaction equation

HRID 1926445 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]([NH2:36])=[C:23]([N:25]4[CH2:34][CH2:33][C:32]5[C:27](=[CH:28][CH:29]=[CH:30][C:31]=5[Cl:35])[CH2:26]4)[CH:24]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CO.CCOCC>[Cl:35][C:31]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:32]=1[CH2:33][CH2:34][N:25]([C:23]1[C:22]([NH2:36])=[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)[CH2:26]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67521840HCID 67521840, compound

Product 1

HCID 67521041HCID 67521041, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

4-{4-[6-Amino-5-(5-chloro-3,4-dihydro-1H-isoquinolin-2-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (26 mg, 0.051 mmol) was dissolved in MeOH (20 mL), 1.0 M of HCl in Et2O (20 mL) was added, and the mixture was stirred at rt overnight. The solvent was removed in vacuo to give the title compound as a brown solid. 1H NMR (400 MHz, CD3OD): δ=2.32-2.39 (m, 4H), 3.11 (t, J=6.0 Hz, 2H), 3.22-3.32 (m, 2H), 3.42 (t, J=6.0 Hz, 2H), 3.59 (d, J=13.2 Hz, 2H), 4.27 (s, 2H), 4.58-4.68 (m, 1H), 7.16 (d, J=7.6 Hz, 1H), 7.22 (t, J=8.0 Hz, 1H), 7.32 (d, J=8.0 Hz, 1H), 7.97 (s, 1H), 7.98 (s, 1H), 8.33 (s, 1H). MS(ES+): m/z=409.10/411.08 (46/18) [MH+]. HPLC: tR=2.25 min (ZQ2, polar—5 min).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1824184f8866427ead89b10e96b2d26f
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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