Imidazole → HCID 22098617, compound

HRID 266207Notes

Reaction equation

[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].N1C=CN=C1.[NH2:18][C:19]1[CH:27]=[CH:26][C:22]([CH2:23][C:24]#[N:25])=[CH:21][CH:20]=1.[OH:28][CH2:29][CH2:30][NH:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][C:39]([O:41][CH3:42])=[O:40])=[CH:34][CH:33]=1>O1CCCC1>[C:24]([CH2:23][C:22]1[CH:26]=[CH:27][C:19]([NH:18][C:1]([N:31]([CH2:30][CH2:29][OH:28])[C:32]2[CH:37]=[CH:36][C:35]([CH2:38][C:39]([O:41][CH3:42])=[O:40])=[CH:34][CH:33]=2)=[O:2])=[CH:20][CH:21]=1)#[N:25]

Participants

Conditions

Temperature: 0 °C

Procedure

1.46 g of carbonyldiimidazole and 1.04 g of imidazole were dissolved in 20 ml of tetrahydrofuran. The mixture was cooled to 0° C. and 1.18 g of 4-amino-benzylcyanide were added. After about 3 minutes a solution of methyl 4-[(2-hydroxy-ethyl)-amino]-phenylacetate in 7 ml of tetrahydrofuran was rapidly added dropwise, the ice cooling was taken away and the mixture was stirred for 16 hours at ambient temperature (a precipitate formed initially was filtered off). The mixture was concentrated down, the residue was taken up in ethyl acetate, washed with 1N hydrochloric acid and water and the organic phase was evaporated down. The residue was purified by chromatography on silica gel (eluant: ethyl acetate/methylene chloride=1:1).

Workup

customformed initially
filtrationwas filtered off)
concentrationThe mixture was concentrated down
washwashed with 1N hydrochloric acid and water
customthe organic phase was evaporated down
customThe residue was purified by chromatography on silica gel (eluant: ethyl acetate/methylene chloride=1:1)

Sources & evidence

ORD record: ord-5c3c380d698f460c92de8a37fc217912
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05650424

Reaction notes

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