Hexahydro-1,4-diazepine → HCID 10109988, compound

HRID 1282306Notes

Reaction equation

HRID 1282306 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[N:11][C:10]2[C:9]([C:15](Cl)=[O:16])=[C:8]([CH3:18])[C:7]([N+:19]([O-:21])=[O:20])=[CH:6][C:5]=2[N:4]=1.[NH:22]1[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>>[N:22]1([C:15]([C:9]2[C:8]([CH3:18])=[C:7]([N+:19]([O-:21])=[O:20])[CH:6]=[C:5]3[C:10]=2[N:11]=[C:12]([O:13][CH3:14])[C:3]([O:2][CH3:1])=[N:4]3)=[O:16])[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 10805016HCID 10805016, compound

Product 1

HCID 10109988HCID 10109988, compound

Procedure

Prepared from 2,3-dimethoxy-6-methyl-7-nitro-quinoxaline-5-carbonyl chloride (13) 250 mg (0.80 mmol) and homopiperazine 160 mg (1.60 mmol). Reaction was continued for 30 hours, and the crude product was eluted through a flash column (8% methanol in chloroform), 260 mg (87%), mp 141-143° C.; 1H NMR (CDCl3): δ 8.29 (s, 1H), 4.03 (s, 3H), 3.93 (br s, 7H), 3.02 (br s, 2H), 2.82 (t, 2H, J=5.4, J=5.6 Hz), 2.54 (s, 3H), 1.88 (t, 2H, J=5.6, 5.4 Hz), 1.79 (bs, 1H); MS (APCI): m/z 376 (M+H). Anal. Calcd. for C17H21N5O5: C, 54.39; H, 5.64; N, 18.66. Found: C, 54.07; H, 5.57; N, 18.24.

Workup

  1. customReaction
  2. washthe crude product was eluted through a flash column (8% methanol in chloroform), 260 mg (87%), mp 141-143° C.

Sources & evidence

ORD record
ord-0af08146926440298b6e729ab508a3df
Source dataset
uspto-grants-2002_09
Patent number
US06455698B1

Reaction notes

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