Sodium Iodide → HCID 67264467, compound

HRID 1687369Notes

Reaction equation

HRID 1687369 reaction equation
[CH3:1][O:2][C:3]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:6]2[N:7]([CH3:13])[C:8](=[O:12])[CH2:9][NH:10][CH2:11][C:5]=2[CH:4]=1.[CH:19]1([CH2:22]Br)[CH2:21][CH2:20]1.[I-].[Na+].C(N(CC)C(C)C)(C)C.CN(C)C=O>>[CH:19]1([CH2:22][N:10]2[CH2:11][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:6]=3[N:7]([CH3:13])[C:8](=[O:12])[CH2:9]2)[CH2:21][CH2:20]1

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 81503BromomethylcyclopropaneHCID 81531DiisopropylethylamineHCID 67263977HCID 67263977, compound

Product 1

HCID 67264467HCID 67264467, compound

Procedure

A mixture of 7-Methoxy-1-methyl-8-nitro-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (0.50 g, 0.0020 mol), [B] Cyclopropylmethyl bromide (0.55 mL, 0.0057 mol), Sodium iodide (0.003 g, 0.00002 mol) and N,N-Diisopropylethylamine (0.87 mL, 0.0050 mol) in N,N-Dimethylformamide (4 mL, 0.05 mol) was reacted in an analogous manner to example 743-C to give 4-Cyclopropylmethyl-7-methoxy-1-methyl-8-nitro-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one as a red oil. (0.56 g, 92%). LCMS (m/e) 306 (M+1); 1H-NMR (DMSO, 400 MHz) δ 7.92 (s, 1H), 7.44 (s, 1H), 3.95 (s, 3H), 3.66 (s, 2H), 3.26 (s, 2H), 3.13 (s, 2H), 2.89 (s, 1H), 2.73 s, 1H), 2.44-2.42 (d, 2H, J=6.57 Hz), 1.30-1.20 (br, 1H), 0.95-0.87 (br, 2H), 0.50 (d, 2H, J=7.83 Hz), 0.18-0.16 (d, 2H, J=4.80 Hz).

Workup

  1. customwas reacted in an analogous manner to example 743-C

Sources & evidence

ORD record
ord-5aace4336c2e43eaa4ca462617ea24c3
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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