Hydrochloric Acid → 4-tert-Butyl-2-((2-methyl-3-(4-methyl-6-(4-(morpholine-4-carbonyl)-phenylamino)-5-oxo-4,5-dihydropyrazin-2-yl)phenylamino)methyl)benzoic Acid

HRID 1772072Notes

Reaction equation

[C:1]([C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11]CC)=[O:10])=[C:7]([CH2:16][NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[N:25]=[C:26]([NH:32][C:33]4[CH:38]=[CH:37][C:36]([C:39]([N:41]5[CH2:46][CH2:45][O:44][CH2:43][CH2:42]5)=[O:40])=[CH:35][CH:34]=4)[C:27](=[O:31])[N:28]([CH3:30])[CH:29]=3)[C:19]=2[CH3:47])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1.CCO.O>[C:1]([C:5]1[CH:15]=[CH:14][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH2:16][NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[N:25]=[C:26]([NH:32][C:33]4[CH:38]=[CH:37][C:36]([C:39]([N:41]5[CH2:46][CH2:45][O:44][CH2:43][CH2:42]5)=[O:40])=[CH:35][CH:34]=4)[C:27](=[O:31])[N:28]([CH3:30])[CH:29]=3)[C:19]=2[CH3:47])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To 25 mL round bottom flask charged with ester 101h (100 mg, 0.16 mmol) and LiOH (20 mg, 0.47 mmol) in THF (2 mL), EtOH (2 mL) and H2O (2 mL). After the mixture was stirred at 60° C. for 16 h, the pH was adjusted to 7 with aqueous 1M HCl. The aqueous phase was extracted with EtOAc (2×10 mL), and the combined organic extracts were washed with brine (10 mL), dried with Na2SO4 and concentrated. The crude 101i (97 mg, 99%) was used without further purification.

Workup

extractionThe aqueous phase was extracted with EtOAc (2×10 mL)
washthe combined organic extracts were washed with brine (10 mL)
dry with materialdried with Na2SO4
concentrationconcentrated
customThe crude 101i (97 mg, 99%) was used without further purification

Sources & evidence

ORD record: ord-2c2685f96f5c4cd980be8842fd2f4686
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249123B2

Reaction notes

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