Nitrogen → HCID 20515453, compound

HRID 1902481Notes

Reaction equation

[H-].[Na+].[CH3:3][N:4]1[C:13]2[C:12](=[O:14])[NH:11][C:10]3[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=3[NH:8][C:7]=2[CH:6]=[C:5]1[CH3:19].N#N.[CH3:22]I>CS(C)=O.O1CCCC1>[CH3:3][N:4]1[C:13]2[C:12](=[O:14])[N:11]([CH3:22])[C:10]3[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=3[NH:8][C:7]=2[CH:6]=[C:5]1[CH3:19]

Participants

Conditions

Temperature: 5 °C

Procedure

0.33 g (0.011 mole) of 80% sodium hydride (in paraffin) are added to a cold solution (5° C.) of 2.3 g (0.01 mole) of 1,2-dimethyl-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]benzodiazepin-10-one in 20 ml of dry dimethylsulfoxide and 20 ml of tetrahydrofuran under an inert gas atmosphere (N2). The mixture is stirred for 30 minutes and is allowed to come to room temperature (30 minutes). Thereafter, it is again cooled to 5° C. and 1.4 g (0.01 mole) of methyl iodide, dissolved in 5 ml of dry tetrahydrofuran, are added dropwise. After the mixture has been stirred at 35° C. for 2 hours, 50 ml of ice-water are added, and the mixture is extracted several times with ethyl acetate. The combined extracts are concentrated in vacuo, and the residue is chromatographed on neutral silica gel (methylene chloride/methanol), yield: 1.7 g.

Workup

customto come to room temperature
custom(30 minutes)
additionare added dropwise
stirringAfter the mixture has been stirred at 35° C. for 2 hours
extractionthe mixture is extracted several times with ethyl acetate
concentrationThe combined extracts are concentrated in vacuo
customthe residue is chromatographed on neutral silica gel (methylene chloride/methanol), yield: 1.7 g

Sources & evidence

ORD record: ord-eac290233fd4478ea18c8c1b5088991d
Source dataset: uspto-grants-1982_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04363816

Reaction notes

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