Imidazole → HCID 86588759, compound

HRID 392982Notes

Reaction equation

[C:1]([CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[C:10]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[N:14]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:11]2=[N:12][CH:13]=1)=[O:7])#[N:2].N1C=CN=C1.[Si:35](Cl)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].C(OCC)(=O)C>CN(C)C=O>[C:1]([CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[C:10]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])=[CH:19][CH:18]=3)[N:14]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:11]2=[N:12][CH:13]=1)=[O:7])#[N:2]

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of intermediate 60 (1.5 g, 3.85 mmol) in dimethylformamide (5 mL) was added imidazole (0.917 g, 13.5 mmol) and tert-butyldimethylsilyl chloride (0.870 g, 5.77 mmol). The reaction mixture was stirred at 35° C. for 20 h, and then ethyl acetate (100 mL) was added. The resulting organic phase was washed with water (4×20 mL) and brine (1×) and then dried (Na2SO4). After concentrating on a rotary evaporator the resulting residue was purified by column chromatography (silica gel, 1:1 hexanes/ethyl acetate-3:7 hexanes/ethyl acetate) to afford intermediate 61 as a white solid (1.6 g, 83%). ESI-MS m/e 504.0 (M+1).

Workup

washThe resulting organic phase was washed with water (4×20 mL) and brine (1×)
dry with materialdried (Na2SO4)
concentrationAfter concentrating on a rotary evaporator the resulting residue
customwas purified by column chromatography (silica gel, 1:1 hexanes/ethyl acetate-3:7 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-c3ccb5ebb1c94afdb9c246dc3bd1f9fa
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06803374B2

Reaction notes

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