Ammonia → HCID 10134442, compound

HRID 1297134Notes

Reaction equation

HRID 1297134 reaction equation
[CH2:1]([N:3]1[C:9]2[CH:10]=[C:11]([O:16][CH3:17])[C:12]([O:14][CH3:15])=[CH:13][C:8]=2[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:6][CH:5]([CH2:24][C:25](OCC)=[O:26])[C:4]1=[O:30])[CH3:2].[NH3:31]>CO>[CH2:1]([N:3]1[C:9]2[CH:10]=[C:11]([O:16][CH3:17])[C:12]([O:14][CH3:15])=[CH:13][C:8]=2[C:7]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[N:6][CH:5]([CH2:24][C:25]([NH2:31])=[O:26])[C:4]1=[O:30])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10179764HCID 10179764, compound

Product 1

HCID 10134442HCID 10134442, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Stir at 0° C. under an inert atmosphere for 48 hours, 70 mg (0.17 mmol) of ethyl (1-ethyl-7,8-dimethoxy-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl)acetate (IIbv) and 1.5 ml of methanol at 35% molar saturation with NH3. Evaporate to dryness. Purify by silica chromatography (dichloromethane 9/methanol 1). Recrystallize in ether. One obtains 12 mg of the abovenamed product as a white powder. Yield: 17%. M: 105–107° C. 1H-NMR (CDCl3, 300 MHz): d 1.10 (t, 3H, CH3), 3.02–3.09 (m, 1H —CH2), 3.22–3.29 (m, 1H —CH2), 3.75 (s, 1H, OCH3), 3.98 (s, 1H, OCH3), 4.01 (AB system, ? d=0.67, JAB=13.9, 2H, —NCH2), 4.13 (t, 1H, CH), 5.52 (s, 1H exchangeable NH2), 6.43 (s, 1H exchangeable NH2), 6.67 (s, 1H Ar), 6.85 (s, 1H Ar), 7.38–7.47 (m, 3H Ar), 7.59–7.62 (m, 2H Ar).

Workup

  1. customEvaporate to dryness
  2. customPurify by silica chromatography (dichloromethane 9/methanol 1)
  3. customRecrystallize in ether

Sources & evidence

ORD record
ord-d90ac2ef6aa34662b43cda96e9130b0d
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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