Lithium Hydroxide → HCID 66693275, compound

HRID 472849Notes

Reaction equation

[C:1]([O:5][CH:6]([C:11]1[C:12]([CH3:34])=[N:13][C:14]2[N:15]([N:29]=[C:30]([CH3:33])[C:31]=2[Cl:32])[C:16]=1[C:17]1[C:18]([CH3:28])=[C:19]2[C:24](=[C:25]([F:27])[CH:26]=1)[O:23][CH2:22][CH2:21][CH2:20]2)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>O1CCOCC1>[C:1]([O:5][CH:6]([C:11]1[C:12]([CH3:34])=[N:13][C:14]2[N:15]([N:29]=[C:30]([CH3:33])[C:31]=2[Cl:32])[C:16]=1[C:17]1[C:18]([CH3:28])=[C:19]2[C:24](=[C:25]([F:27])[CH:26]=1)[O:23][CH2:22][CH2:21][CH2:20]2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 2-tert-butoxy-2-(3-chloro-7-(8-fluoro-5-methylchroman-6-yl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)acetate, (5 mg, 10 umol) in dioxane (0.5 mL) was added 1.0 N LiOH aqueous solution (0.5 mL, 0.5 mmol). The reaction mixture was stirred at 50° C. for 2 h. The reaction mixture was filtered and the filtrate was purified by preparative HPLC to afford (3 mg, 60%) of the title compound. Preparative HPLC condition: Phenomenex Luna C18 30×100 mm S10, 50 to 100% B over 22 min gradient, 6 min hold time, A=10% methanol 90% water 0.1% TFA, B=90% methanol 10% water 0.1% TFA. Flow rate: 40 mL/min. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.03 (9H, br. s.), 1.8 (2H, s), 2.28 (2H, br. s.), 2.52 (3H, s), 2.74 (3H, br. s.), 2.96 (3H, s), 4.29 (2H, br. s.), 4.7 (1H, s), 6.98 (1H, s), 7.96 (1H, s).

Workup

filtrationThe reaction mixture was filtered
customthe filtrate was purified by preparative HPLC

Sources & evidence

ORD record: ord-eb6153cefdfa43698817fc5d4db7d4dc
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633200B2

Reaction notes

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