Cyanamide → HCID 68283425, compound

HRID 1855300Notes

Reaction equation

HRID 1855300 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:24])=[CH:9][C:10]([O:22][CH3:23])=[CH:11][C:12]=3[C:13]2([C:17]2[NH:18][CH:19]=[CH:20][N:21]=2)Cl)=[CH:4][CH:3]=1.[N:25]#[C:26][NH2:27]>O1CCOCC1>[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:24])=[CH:9][C:10]([O:22][CH3:23])=[CH:11][C:12]=3[C:13]32[C:17]2=[N:18][CH:19]=[CH:20][N:21]2[C:26]([NH2:27])=[N:25]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9864CyanamideHCID 68283255HCID 68283255, compound

Product 1

HCID 68283425HCID 68283425, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 2-(7-bromo-9-chloro-4-fluoro-2-methoxy-9H-xanthen-9-yl)-1H-imidazole (10 g, 24.41 mmol) was added a solution of cyanamide (1.539 g, 36.6 mmol) in dioxane (244 mL). The solution was stirred at RT for 30 minutes. The solution was then heated at reflux for 6 hrs until only a product peak was seen by LCMS. The solution was concentrated under vacuum. The solution was quenched with 500 ml of saturated sodium bicarbonate and 500 ml of water, and sonicated for 30 minutes. The product was then collected by filtration. The solid was then triturated with DCM and dried under vacuum to afford 7′-bromo-4′-fluoro-2′-methoxyspiro[imidazo[1,5-a]imidazole-7,9′-xanthen]-5-amine (10 g, 24.4 mmol) as a light brown solid.

Workup

  1. temperatureThe solution was then heated
  2. temperatureat reflux for 6 hrs until only a product peak
  3. concentrationThe solution was concentrated under vacuum
  4. customThe solution was quenched with 500 ml of saturated sodium bicarbonate and 500 ml of water
  5. customsonicated for 30 minutes
  6. filtrationThe product was then collected by filtration
  7. customThe solid was then triturated with DCM
  8. customdried under vacuum

Sources & evidence

ORD record
ord-2c1afc60bfd74b83a7841120db638afa
Source dataset
uspto-grants-2015_02
Patent number
US08962859B2

Reaction notes

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