Methoxymethyl isocyanate → HCID 49869280, compound

HRID 570966Notes

Reaction equation

N([O-])=O.[Na+].NC1NC=NC=1/C=C/C1C=CC(C#N)=CC=1.[CH3:21][O:22][CH2:23][N:24]=[C:25]=[O:26].[N+:27](=[C:29]1[C:33](/[CH:34]=[CH:35]/[C:36]2[CH:43]=[CH:42][C:39]([C:40]#[N:41])=[CH:38][CH:37]=2)=[N:32][CH:31]=[N:30]1)=[N-:28]>O.[H+].[B-](F)(F)(F)F.CS(C)=O>[CH3:21][O:22][CH2:23][N:24]1[C:25](=[O:26])[N:30]2[CH:31]=[N:32][C:33](/[CH:34]=[CH:35]/[C:36]3[CH:43]=[CH:42][C:39]([C:40]#[N:41])=[CH:38][CH:37]=3)=[C:29]2[N:27]=[N:28]1

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

filtrationthe precipitate was filtered from solution
dry with materialdried over P2O5
customThis diazo compound was used without further purification
stirringThe resulting solution was stirred at room temperature for 24 hours
custompurified by column chromatography (5% MeCN/DCM)

Sources & evidence

ORD record: ord-8d55180127e04486a013cab122797415
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024018B2

Reaction notes

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