Sodium Hydroxide → HCID 69673524, compound

HRID 2276331Notes

Reaction equation

[CH3:1][C:2]1[C:14]([CH:15]([CH2:20][CH2:21][CH3:22])[C:16]([O:18]C)=[O:17])=[C:13]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)[N:5]2[N:6]=[C:7]3[C:12]([CH:11]=[CH:10][CH:9]=[CH:8]3)=[C:4]2[N:3]=1.[OH-].[Na+]>CO.C(O)C>[CH3:1][C:2]1[C:14]([CH:15]([CH2:20][CH2:21][CH3:22])[C:16]([OH:18])=[O:17])=[C:13]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)[N:5]2[N:6]=[C:7]3[C:12]([CH:11]=[CH:10][CH:9]=[CH:8]3)=[C:4]2[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 2-(2-methyl-4-p-tolylpyrimido[1,2-b]indazol-3-yl)pentanoate (0.264 g; 0.68 mmol) in a mixture methanol-ethanol (2:1) (21 mL) was added a 5% sodium hydroxide solution (16.3 mL; 20.4 mmol) and the reaction mixture was heated to 60° C. for 18 h. The organic volatiles were removed under reduced pressure and the remaining basic solution was acidified till pH 2 with a 1N hydrochloric acid solution and the aqueous layer was extracted with ethyl acetate. The organics were combined, dried over magnesium sulfate and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of methanol (1-20%) in dichloromethane and by preparative HPLC (method 2) furnished 0.076 g (30%) of 2-(2-methyl-4-p-tolylpyrimido[1,2-b]indazol-3-yl)pentanoic acid as a white solid. ESI/APCI(+): 374 (M+H). ESI/APCI(−): 372 (M−H).

Workup

customThe organic volatiles were removed under reduced pressure
extractionthe aqueous layer was extracted with ethyl acetate
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customPurification by flash chromatography on silica gel using a gradient of methanol (1-20%) in dichloromethane

Sources & evidence

ORD record: ord-07b508e17ccf4e749546c02882cca9f5
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09132129B2

Reaction notes

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