Bis-(1H-imidazol-2-YL)-methanone → HCID 10366967, compound

HRID 1247516Notes

Reaction equation

[C:1](C1NC=CN=1)(C1NC=CN=1)=[O:2].[Cl:13][C:14]1[S:41][C:17]2[NH:18][C:19]([C:21]([NH:23][CH:24]3[CH2:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]([CH2:34][CH:35]([CH2:38][OH:39])[CH2:36][OH:37])[C:25]3=[O:40])=[O:22])=[CH:20][C:16]=2[CH:15]=1>CN(C1C=CN=CC=1)C>[Cl:13][C:14]1[S:41][C:17]2[NH:18][C:19]([C:21]([NH:23][CH:24]3[CH2:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]([CH2:34][CH:35]4[CH2:38][O:39][C:1](=[O:2])[O:37][CH2:36]4)[C:25]3=[O:40])=[O:22])=[CH:20][C:16]=2[CH:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Carbonyl diimidazole (143 mg, 0.88 mmol) was added to 2-chloro-N-{1-[3-hydroxy-2-(hydroxymethyl)propyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide (Example 22; 250 mg, 0.58 mmol) followed by DMAP (2 mg) and the reaction was heated at 50° C. for 4 hours. The reaction was quenched by addition of EtOAc (50 mL) and H2O (10 mL) and the organic layer was separated and washed further with saturated aqueous NaHCO3, 1M HCl (aq.) and brine. The organic layer was then dried (MgSO4), filtered and evaporated. Trituration with hot Et2O (15 mL), cooling and filtration afforded the title compound (182 mg, 0.40 mmol, 68%) as a white solid.

Workup

customThe reaction was quenched by addition of EtOAc (50 mL) and H2O (10 mL)
customthe organic layer was separated
washwashed further with saturated aqueous NaHCO3, 1M HCl (aq.) and brine
dry with materialThe organic layer was then dried (MgSO4)
filtrationfiltered
customevaporated
temperatureTrituration with hot Et2O (15 mL), cooling
filtrationfiltration

Sources & evidence

ORD record: ord-f6f7d8e52f1d4a58ae596a264e08dc79
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129249B2

Reaction notes

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