Hydrochloric Acid → HCID 57829278, compound

HRID 2356693Notes

Reaction equation

HRID 2356693 reaction equation
[C:1]([C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:7][C:6]([N:16]2[C:20](=[O:21])[C:19]([CH3:23])([CH3:22])[N:18]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[NH:32][C:33]3[CH:38]=[CH:37][C:36]([C:39]([CH3:54])([C:47]([O:49]C(C)(C)C)=[O:48])[C:40]([O:42]C(C)(C)C)=[O:41])=[CH:35][CH:34]=3)[C:17]2=[O:55])=[CH:5][CH:4]=1)#[N:2].Cl>O1CCOCC1>[C:1]([C:3]1[C:8]([C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)=[CH:7][C:6]([N:16]2[C:20](=[O:21])[C:19]([CH3:23])([CH3:22])[N:18]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[NH:32][C:33]3[CH:38]=[CH:37][C:36]([C:39]([CH3:54])([C:47]([OH:49])=[O:48])[C:40]([OH:42])=[O:41])=[CH:35][CH:34]=3)[C:17]2=[O:55])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68678558HCID 68678558, compound

Product 1

HCID 57829278HCID 57829278, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The compound of Example 259 was, as described for the preparation of Example 233, obtained via the corresponding tert-butyl ester. The di-tert-butyl ester 259.3 was obtained via the sequence of 236.1 (di-tert-butyl 2-methyl-2-(4-nitrophenyl)-malonate; 1H NMR: 8.22, d, 2H, 7.64, d, 2H, 1.71, s, 3H, 1.41, s, 18H)→236.2 (di-tert-butyl 2-(4-aminophenyl)-2-methylmalonate hydrochloride; molecular weight (free base) 321.19 (C18H27NO4); retention time Rt=1.61 min. [C]; MS (ESI): 322.21 (MH+))→259.3 (di-tert-butyl 2-(4-{2-[3-(6-cyano-4′-fluorobiphenyl-3-yl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-ylmethyl]-5-fluorophenylamino}phenyl)-2-methylmalonate (by reaction with 253.3)). The reaction of the crude product with 4N hydrochloric acid in dioxane afforded compound 259; molecular weight 638.19 (C35H28F2N4O6); retention time Rt=2.59 min. [D]; MS (ESI): 639.30 (MH+).

Sources & evidence

ORD record
ord-f04a836ea1534254b96c7034cd45fe36
Source dataset
uspto-grants-2010_07
Patent number
US07759366B2

Reaction notes

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