Methyl iodide → (3-methylbenzoimidazol-4-yl)-(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]-1'-yl)methanone

HRID 1908177Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([N:12]3[CH2:17][CH2:16][C:15]4([C:29]5[CH:28]=[N:27][N:26]([CH3:30])[C:25]=5[C:24]5[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=5[O:18]4)[CH2:14][CH2:13]3)=[O:11])[C:4]=2[N:3]=[CH:2]1.[H-].[Na+].[CH3:33]I>C1COCC1.CO>[CH3:33][N:3]1[C:4]2[C:9]([C:10]([N:12]3[CH2:17][CH2:16][C:15]4([C:29]5[CH:28]=[N:27][N:26]([CH3:30])[C:25]=5[C:24]5[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=5[O:18]4)[CH2:14][CH2:13]3)=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[CH:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (1H-benzo[d]imidazol-4-yl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone (21 mg, 0.052 mmol) in dry THF (0.2 mL) under N2 was added NaH (1.9 mg, 0.079 mmol) at 0° C. After 30 min, MeI (3.3 μL, 0.052 mmol) was added and the mixture was stirred at 0° C. for 1 h. The reaction mixture was quenched with water and the solvent removed under vacuum to yield a crude residue that was taken up in methanol and purified by reverse phase HPLC to give (3-methylbenzoimidazol-4-yl)-(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone. ESI-MS m/z calc. 413.5. found 414.5 (M+1)+. Retention time: 1.13 minutes (3 min run).

Workup

customThe reaction mixture was quenched with water
customthe solvent removed under vacuum
customto yield a crude residue that
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-880b82afe14d44feb70985f073dc06ea
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598164B2

Reaction notes

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