Methoxymethyl isocyanate → HCID 49869280, compound

Participants

Reaction Conditions

Reaction Steps

Sodium nitrite (40 mg, 0.57 mmol) in water (0.5 mL) was added to a suspension of (E)-4-(2-(5-amino-1H-imidazol-4-yl)vinyl)benzonitrile (100 mg, 0.47 mmol) in 50% HBF4 (2 mL) at 0° C. After stirring at 0° C. for 20 minutes, the precipitate was filtered from solution and dried over P2O5. This diazo compound was used without further purification. Methoxymethyl isocyanate (150 mg, 1.8 mmol) was added to a solution of (E)-4-(2-(4-diazo-4H-imidazol-5-yl)vinyl)benzonitrile (80 mg, 0.36 mmol) in dry DMSO (1 mL) under nitrogen. The resulting solution was stirred at room temperature for 24 hours, then purified by column chromatography (5% MeCN/DCM) to give the title compound as a yellow solid (42 mg, 38%). δH (DMSO-d6) 8.48 (1H, s), 7.81 (1H, d, J=16.0), 7.71 (4H, m), 7.60 (1H, d, J=16.0) 5.72 (2H, s), 3.58 (3H, s); IR (cm−1) 2222 (C≡N), 1631 (C═N); MS (m/z) 309.1121 (C15H13N6O2 (M+1)) requires 309.1100.

Provenance & Evidence