Methyl iodide → HCID 86633915, compound

HRID 1687364Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:6]2[NH:7][C:8](=[O:18])[CH2:9][N:10]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:11][C:5]=2[CH:4]=1.[F-].[Cs+].[C:26](#N)C.CI>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH3:26])[C:8](=[O:18])[CH2:9][N:10]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:11][C:19]=2[C:20]=1[N+:21]([O-:23])=[O:22]

Participants

Reactant 4

HCID 6328Methyl iodide

HCID 6342Acetonitrile

HCID 25953Cesium fluoride

HCID 86633914HCID 86633914, compound

Product 1

HCID 86633915HCID 86633915, compoundYield 91.5%

Procedure

A mixture of 7-Methoxy-8-nitro-4-(2,2,2-trifluoro-acetyl)-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (3.00 g, 0.00900 mol), Cesium fluoride (3.40 g, 0.022 mol), Acetonitrile (100 mL, 2 mol) and Methyl iodide (1.68 mL, 0.026 mol) were reacted in an analogous manner to example 736-C to give 7-Methoxy-1-methyl-6-nitro-4-(2,2,2-trifluoro-acetyl)-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one as a tan solid (2.86 g, 91%). Mp 71-74° C.; LCMS (m/e) 348 (M+1); 1H-NMR (DMSO, 400 MHz) δ 8.06 (s, 0.5H), 805 (s, 1H), 7.75 (s, 1H), 7.65 (s, 0.5H), 4.77 (s, 1H), 4.73 (s, 2H), 4.09 (s, 1H), 4.03 (s, 2H), 3.96-95 (s, 3H).

Workup

customwere reacted in an analogous manner to example 736-C

Sources & evidence

ORD record: ord-037e798650bd426f91ee821d117dc287
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148391B2

Reaction notes

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