2-Aminothiazole → HCID 11152144, compound

HRID 2264383Notes

Reaction equation

HRID 2264383 reaction equation
Cl[C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]2[C:12](=[O:20])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[N:19]=[C:4]2[N:3]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[NH2:63][C:64]1[S:65][CH:66]=[CH:67][N:68]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1.C1(C)C=CC=CC=1>[S:65]1[CH:66]=[CH:67][N:68]=[C:64]1[NH:63][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]2[C:12](=[O:20])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[N:19]=[C:4]2[N:3]=1

Participants

7

Reactant 4

HCID 21552-AminothiazoleHCID 10340Sodium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 68686094HCID 68686094, compound

Product 1

HCID 11152144HCID 11152144, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 21840791Dioxane tolueneSolvent

Procedure

A pressure tube was charged with 5-chloro-quinazolino[3,2-a]quinazolin-12-one (200 mg, 0.71 mmol), Pd2(dba)3 (25 mg, 0.028 mmol), Xantphos (25 mg, 0.043 mmol), 2-aminothiazole (71 mg, 0.85 mmol), Na2CO3 (fine powder, 71 mg, 0.85 mmol) and anhydrous dioxane/toluene (1:1, 5 mL). The mixture was stirred with heating at 100 deg C. for 17 hours. After this period the mixture was cooled, concentrated in vacuo and purified by preparative chromatography, to yield the desired product (TFA salt) as a yellow powder (130 mg).

Workup

  1. temperaturewith heating at 100 deg C
  2. temperatureAfter this period the mixture was cooled
  3. concentrationconcentrated in vacuo
  4. custompurified by preparative chromatography

Sources & evidence

ORD record
ord-71f4093c2f374558a18760139c448643
Source dataset
uspto-grants-2010_12
Patent number
US07855214B2

Reaction notes

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