HCID 24890194, compound → HCID 24889002, compound

HRID 1507067Notes

Reaction equation

HRID 1507067 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:33])[C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=3)=[CH:20][C:19]=2[C:34]2[N:35]([CH3:40])[N:36]=[CH:37][C:38]=2[Cl:39])[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[Cl:39][C:38]1[CH:37]=[N:36][N:35]([CH3:40])[C:34]=1[C:19]1[CH:20]=[C:21]([NH:24][C:25](=[O:33])[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)[CH:22]=[CH:23][C:18]=1[O:17][CH2:16][CH2:15][NH:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 24890194HCID 24890194, compound

Product 1

HCID 24889002HCID 24889002, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-{2-[2-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-(3-fluoro-benzoylamino)-phenoxy]-ethylamino}-piperidine-1-carboxylic acid tert-butyl ester (0.035 g, 0.061 mmol) in 4 M HCl in dioxane (2.2 mL) was shaken on a rotary stirrer for 3 hours. The reaction was concentrated and purified by RP-HPLC. Lyophilization afforded a TFA salt as a pale solid (0.021 g, 48%). LCMS m/z (%)=472 (M+H, 35Cl, 100), 474 (M+H, 37Cl, 40). 1H NMR (400 MHz, DMSO-d6) δ 10.40 (s, 1H), 7.96 (dd, J=2.6, 9.0 Hz, 1H), 7.81 (d, J=8.0 Hz, 1H), 7.77 (m, 1H), 7.73 (d, J=2.6 Hz, 1H), 7.68 (s, 1H), 7.64-7.57 (m, 1H) 7.47 (dt, J=2.6, 8.8 Hz, 1H), 7.30 (d, J=9.1 Hz, 1H), 4.37-4.22 (m, 2H), 3.69 (s, 3H), 3.42-3.28 (m, 4H), 3.22-3.10 (m, 1H), 2.86-2.70 (m, 2H), 2.05 (d, J=12.1 Hz, 2H), 1.65-1.50 (m, 2H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-29ba564301db4575a0b4796df0441880
Source dataset
uspto-grants-2015_12
Patent number
US09221755B2

Reaction notes

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