Potassium Carbonate → LY-301664

HRID 131302Notes

Reaction equation

HRID 131302 reaction equation
Cl.[CH3:2][C:3]1[S:12][C:11]2[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[N:7]=[C:6](N)[C:5]=2[CH:4]=1.C(=O)([O-])[O-:19].[K+].[K+]>O.C(O)C>[CH3:2][C:3]1[S:12][C:11]2[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[NH:7][C:6](=[O:19])[C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 13552565010H-Thieno[2,3-b][1,5]benzodiazepin-4-amine, 2-methyl-, hydrochloride (1:1)

Product 1

HCID 29978685LY-301664

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Combine 2-methyl-4H-3-thia-4,9-diazabenzo[f]azulene-10-ylamine hydrochloride (U.S. Pat. No. 5,229,382) (50 g, 0.19 mol) and solid potassium carbonate (182 g, 1.32 mol) in a mixture of water (1 L) and ethanol (450 mL) and heat at 85° C. for 48 h. Cool to room temperature, and place in ice bath for 2 h. The desired material precipitates out as a yellow solid. Collect solid by filtration, wash with cold water, air-dry for a few minutes and place in the vacuum oven at 45° C. for 48 h to obtain 41.9 g of the title compound, which can be used directly on the next step without further purification: mass spectrum (APCI): m/z=231.0 (M+1).

Workup

  1. temperatureCool to room temperature
  2. customThe desired material precipitates out as a yellow solid
  3. customCollect solid
  4. filtrationby filtration
  5. washwash with cold water
  6. customair-dry for a few minutes

Sources & evidence

ORD record
ord-5ba7b7cf91e54025b69565ace79f0909
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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