Calciumoxide → HCID 18516277, compound

HRID 1977430Notes

Reaction equation

HRID 1977430 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[S:23][C:10]2=[CH:11][N:12]=[CH:13][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[C:9]2[CH:8]=1)=O.[O-2].[Ca+2]>C1(OC2C=CC=CC=2)C=CC=CC=1>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:14]2[CH:13]=[N:12][CH:11]=[C:10]3[S:23][C:7]([C:5]4[NH:4][CH2:3][CH2:2][N:1]=4)=[CH:8][C:9]=23)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6850728CalciumoxideHCID 10154743HCID 10154743, compound

Product 1

HCID 18516277HCID 18516277, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A suspension of Example 154 (0.15 g, 0.43 mmol) and calcium oxide (0.12 g, 2.15 mmol) in phenyl ether (10 mL) was heated to 220-250° C. The reaction was stirred 45 minutes over which reaction volume decreased due to evaporation of solvent. The reaction was cooled to room temperature and diluted with 10% MeOH/dichloromethane (25 mnL) then filtered. The filtrate was concentrated and residue was purified by preparative HPLC using a gradient of 30%-90% acetonitrile/water +0.1% TFA over 40 minutes. The product containing fractions were combined and neutralized with sat NaHCO3. The product crystalized upon standing for 3 days and was collected by filtration, and dried in a desiccator to yield the title compound as a tan needles (23 mg, 16%).

Workup

  1. customdecreased due to evaporation of solvent
  2. additiondiluted with 10% MeOH/dichloromethane (25 mnL)
  3. filtrationthen filtered
  4. concentrationThe filtrate was concentrated
  5. customresidue was purified by preparative HPLC
  6. customover 40 minutes
  7. additionThe product containing fractions
  8. customThe product crystalized
  9. waitupon standing for 3 days
  10. filtrationwas collected by filtration
  11. customdried in a desiccator

Sources & evidence

ORD record
ord-fec709fc14894dc280c524ea52f77740
Source dataset
uspto-grants-2001_05
Patent number
US06232320B1

Reaction notes

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