Water → HCID 59405025, compound

HRID 1892181Notes

Reaction equation

HRID 1892181 reaction equation
[Cl:1][C:2]1[C:18]([I:19])=[CH:17][C:5]2[C:6](=O)/[C:7](=[CH:12]\N(C)C)/[CH2:8][C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1.Cl.[NH2:21][C:22]([NH2:24])=[NH:23].C(=O)([O-])[O-].[K+].[K+].O>CCO>[NH2:23][C:22]1[N:24]=[CH:12][C:7]2[CH2:8][C:9](=[O:11])[NH:10][C:4]3[CH:3]=[C:2]([Cl:1])[C:18]([I:19])=[CH:17][C:5]=3[C:6]=2[N:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 58476643HCID 58476643, compound

Product 1

HCID 59405025HCID 59405025, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of (4Z)-8-chloro-4-[(dimethylamino)methylene]-7-iodo-3,4-dihydro-1H-1-benzazepine-2,5-dione (9.50 g, 24.3 mmol), guanidine hydrochloride (2.56 g, 26.8 mmol), and potassium carbonate (11.1 g, 80.3 mmol) in EtOH (143) was allowed to stir while heating at 70° C. in a sealed reaction vessel. After 19 h, the reaction mixture was allowed to cool to room temperature then added to water (200 mL) and allowed to stir for 1 h. The resulting tan solid was collected via suction filtration, washed with water, and dried in a vacuum oven to give 2-amino-9-chloro-10-iodo-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (7.69 g, 82%). LCMS (FA): m/z=387 (M+H).

Workup

  1. temperatureto cool to room temperature
  2. stirringto stir for 1 h
  3. filtrationThe resulting tan solid was collected via suction filtration
  4. washwashed with water
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-25093cef4b7646bab3762fcd27589360
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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