HCID 89973651, compound → HCID 123532983, compound

HRID 1400759Notes

Reaction equation

HRID 1400759 reaction equation
[CH2:1]([O:4][C:5]1([CH3:52])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([C:20]4[CH:21]=[C:22]([C:26]5[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:27]=5[O:33][CH:34]([CH:36]([CH3:39])C=C)[CH3:35])[CH:23]=[CH:24][CH:25]=4)[CH:19]=[C:15]3[N:14]=[C:13]([CH3:40])[C:12]=2[C@H:41]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])[C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:7][CH2:6]1)[CH:2]=[CH2:3]>ClCCCl.[Cu]I.C1(C)C=C(C)C=C(C)C=1N1CCN(C2C(C)=CC(C)=CC=2C)C1=[Ru](Cl)(Cl)=CC1C=CC=CC=1OC(C)C>[C:48]([O:47][C@@H:41]([C:12]1[C:13]([CH3:40])=[N:14][C:15]2=[CH:19][C:18]3=[N:17][N:16]2[C:11]=1[N:8]1[CH2:9][CH2:10][C:5]([CH3:52])([O:4][CH2:1][CH:2]=[CH:3][CH:36]([CH3:39])[CH:34]([CH3:35])[O:33][C:27]2[CH:28]=[CH:29][C:30]([CH3:32])=[CH:31][C:26]=2[C:22]2[CH:21]=[C:20]3[CH:25]=[CH:24][CH:23]=2)[CH2:6][CH2:7]1)[C:42]([O:44][CH2:45][CH3:46])=[O:43])([CH3:51])([CH3:49])[CH3:50]

Participants

5

Reactant 1

HCID 89973651HCID 89973651, compound

Product 1

HCID 123532983HCID 123532983, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11763533(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)rutheniumCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of (2S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-5-methyl-2-(5′-methyl-2′-((3-methylpent-4-en-2-yl)oxy)-[1,1′-biphenyl]-3-yl)pyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (250 mg, 0.353 mmol) and CuI (67.2 mg, 0.353 mmol) in DCE (200 mL) at 70° C. was added (1,3-dimesitylimidazolidin-2-ylidene)(2-isopropoxybenzylidene)ruthenium(VI) chloride (22.10 mg, 0.035 mmol) and the resulting mixture was refluxed for 2 h. At this point LCMS indicates completion of reaction. Mixture was then concentrated and used as is in the next step without further purification. LCMS (M+H)=681.4.

Workup

  1. temperaturethe resulting mixture was refluxed for 2 h
  2. customcompletion of reaction
  3. concentrationMixture was then concentrated
  4. customas is in the next step without further purification

Sources & evidence

ORD record
ord-c2f4280ed2b5463d9649f877ee9172dd
Source dataset
uspto-grants-2014_12
Patent number
US08906929B2

Reaction notes

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