Sodium Iodide → HCID 90113565, compound

HRID 1504227Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[NH:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH2:18][N:19]1[CH:24]=[CH:23][C:22]2[O:25][C:26]([CH3:28])=[CH:27][C:21]=2[C:20]1=[O:29].Cl[CH2:31][CH2:32][O:33][C:34]1[CH:51]=[CH:50][C:37]2[N:38]([CH2:48][CH3:49])[C:39](=[O:47])[C:40]([CH3:46])([CH3:45])[C:41](=[O:44])[N:42]([CH3:43])[C:36]=2[CH:35]=1>CN(C=O)C>[CH2:48]([N:38]1[C:39](=[O:47])[C:40]([CH3:46])([CH3:45])[C:41](=[O:44])[N:42]([CH3:43])[C:36]2[CH:35]=[C:34]([O:33][CH2:32][CH2:31][N:9]3[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[N:11]=[C:10]3[CH2:18][N:19]3[CH:24]=[CH:23][C:22]4[O:25][C:26]([CH3:28])=[CH:27][C:21]=4[C:20]3=[O:29])[CH:51]=[CH:50][C:37]1=2)[CH3:49]

Participants

Conditions

Temperature: 65 °C

Procedure

Potassium carbonate(0.58 g), sodium iodide(0.21 g), and 5-(1H-benzimidazol-2-ylmethyl)-2-methyl-5H-furo[3,2-c]pyridine-4-one(0.39 g) were added to a DMF solution(30 ml) of 7-(2-chloroethoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione(0.47 g). The mixture was stirred at 65° C. overnight. The mixture was further stirred at 100° C. overnight. After the reaction mixture was condensed under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate: methanol=95:5→85:15). The purified product was condensed to dryness under reduced pressure to give the title compound(0.44 g) as a white amorphous solid.

Workup

stirringThe mixture was further stirred at 100° C. overnight
customcondensed under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate: methanol=95:5→85:15)
customcondensed to dryness under reduced pressure

Sources & evidence

ORD record: ord-73d93c076ad34cf984a0dedef81b90a2
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212187B2

Reaction notes

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