Ammonia → HCID 67979438, compound

HRID 1965146Notes

Reaction equation

HRID 1965146 reaction equation
[Br:1][C:2]1[CH:25]=[C:24]2[C:5]([CH2:6][C:7]3([C:17]42[NH:21][C:20](=S)[C:19]([CH3:23])=[N:18]4)[CH2:12][CH2:11][C:10]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:9][CH2:8]3)=[CH:4][CH:3]=1.[NH3:26]>>[Br:1][C:2]1[CH:25]=[C:24]2[C:5]([CH2:6][C:7]3([C:17]42[N:21]=[C:20]([NH2:26])[C:19]([CH3:23])=[N:18]4)[CH2:12][CH2:11][C:10]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:9][CH2:8]3)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86667281HCID 86667281, compound

Product 1

HCID 67979438HCID 67979438, compoundYield 118.1%

Conditions

Temperature
110 °C

Procedure

6″-Bromo-5′″-methyl-3″H-trispiro[1,3-dioxolane-2,1′-cyclohexane-4′,2″-indene-1″,2′″-imidazole]-4″(3′″H)-thione (Example 115 Step 4, 0.5 g, 1.19 mmol) was taken up in ammonia (7 M in MeOH, 15 mL, 105 mmol) and the resulting mixture was heated in the microwave reactor at 110° C. for 30 min. The solvent was evaporated in vacuo and the same procedure (addition of ammonia, heating and evaporation) was repeated 3 times. The solvent was evaporated to yield the title compound (0.568 g, quantitative yield) that was used without further purification: 1H NMR (500 MHz, CDCl3) δ ppm 1.35-1.49 (m, 2 H), 1.61 (d, 2 H), 1.69-1.81 (m, 2 H), 2.33 (s, 3 H), 3.14 (s, 2 H), 3.87-3.98 (m, 4 H), 6.88 (d, 1 H), 7.19 (d, 1 H), 7.35 (dd, 1 H); MS (ES+) m/z 404 [M+H]+.

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionthe same procedure (addition of ammonia, heating and evaporation)
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9c4d4941157f46bbb9489f11d830102b
Source dataset
uspto-grants-2013_04
Patent number
US08415483B2

Reaction notes

Loading…