1-Methyl-2-imidazolecarboxaldehyde → HCID 68313314, compound

HRID 1843129Notes

Reaction equation

O=[C:2]1[NH:10][C:9]2[C:4](=[N:5][C:6]([C:11]3[CH:12]=[N:13][N:14]4[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][C:15]=34)=[N:7][CH:8]=2)[N:3]1[CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.[CH3:28][N:29]1[CH:33]=[CH:32][N:31]=[C:30]1C=O>CC(O)=O.CC(N(C)C)=O>[CH3:28][N:29]1[CH:33]=[CH:32][N:31]=[C:30]1[C:2]1[N:3]([CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[C:4]2[C:9]([N:10]=1)=[CH:8][N:7]=[C:6]([C:11]1[CH:12]=[N:13][N:14]3[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][C:15]=13)[N:5]=2

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of the compound obtained in example 1 section d (100 mg, 0.30 mmol) in AcOH (0.025 mL) and DMA (2.5 mL), 1-methyl-1H-imidazole-2-carbaldehyde (46 mg, 0.42 mmol) was added. The reaction mixture was stirred in a sealed tube at 140° C. for 19 h. The crude mixture was quenched with H2O (10 mL), extracted with EtOAc (3×10 mL) and the combined organic phases were dried over anhydrous Na2SO4, filtered and concentrated. The crude product thus obtained was chromatographed over silica gel using hexanes/EtOAc mixtures of increasing polarity as eluent, to afford 40 mg of the desired compound (31% yield).

Workup

customThe crude mixture was quenched with H2O (10 mL)
extractionextracted with EtOAc (3×10 mL)
dry with materialthe combined organic phases were dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product thus obtained
customwas chromatographed over silica gel
temperatureof increasing polarity as eluent

Sources & evidence

ORD record: ord-995e10bd407146f698ba9d27a4a18717
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946257B2

Reaction notes

Loading…