2-Aminothiazole → HCID 86649623, compound

HRID 1897935Notes

Reaction equation

HRID 1897935 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][C:9]2([OH:22])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:4][CH:3]=1.[NH2:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)(Cl)Cl.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].C1(C)C=CC=CC=1>[OH:22][C:9]1([CH2:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([NH:23][C:24]3[S:25][CH:26]=[CH:27][N:28]=3)[N:7]=2)[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1

Participants

9

Reactant 5

HCID 21552-AminothiazoleHCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)2×HCID 57366393HCID 57366393, compound

Product 1

HCID 86649623HCID 86649623, compound

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalyst2×HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 50.3 mg of tert-butyl 4((6-chloropyridin-2-yl)methyl)-4-hydroxypiperidine-1-carboxylate, 19.3 mg of 2-aminothiazole, 9.0 mg of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 4.8 mg of bis(dibenzylideneacetone)palladium(0), 25.2 mg of sodium carbonate and 0.77 ml of toluene was stirred at 100° C. overnight and 120° C. overnight. 156.6 mg of cesium carbonate, 94.4 mg of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene and 47.1 mg of bis(dibenzylideneacetone)palladium(0) were added to the reaction mixture, followed by stirring the reaction mixture at 130° C. overnight. The reaction mixture was cooled to room temperature, and diluted with chloroform. An insoluble matter was filtered off using Celite, and the filtrate was concentrated in vacuo. The resulting residue was purified by a preparative thin-layer chromatography (Kieselgel™ 60F254, Art5744 (Merck), chloroform/methanol=10/1) to give the title compound as a brown oil.

Workup

  1. stirringby stirring the reaction mixture at 130° C. overnight
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationAn insoluble matter was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe resulting residue was purified by a preparative thin-layer chromatography (Kieselgel™ 60F254, Art5744 (Merck), chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-114a40bf5c464761b5cae7ac4fc4ed1a
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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