Sodium Hydroxide → HCID 86575567, compound

HRID 574345Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 2-tert-butoxy-2-(7-(4,4-dimethylpiperidin-1-yl)-5-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetate (25 mg, 0.054 mmol) in dioxane (0.8 ml) was added sodium hydroxide (0.8 mL, 0.8 mmol). The resulting mixture was warmed to 50° C. and stirred for 4 h. then filtered and purified by Pre-HPLC to afford 2-tert-butoxy-2-(7-(4,4-dimethylpiperidin-1-yl)-5-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetic acid (18 mg, 0.039 mmol, 72.8% yield). 1H-NMR (400 MHz, CDCl3) δ 1.17 (6 H, s), 1.30 (9 H, s), 1.57-1.61 (2 H, m), 1.70-1.72 (2 H, m), 2.70 (3H, s), 5.83 (1 H, s), 7.49-7.54 (3 H, m), 8.35-8.37 (2 H, m).

Workup

filtrationthen filtered
custompurified by Pre-HPLC

Sources & evidence

ORD record: ord-0b61737b36e749c0aa6bbf35f7ec3cff
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034882B2

Reaction notes

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