HCID 118318780, compound → HCID 124022251, compound

HRID 921100Notes

Reaction equation

[CH2:1]([C:4]1[CH:44]=[CH:43][CH:42]=[CH:41][C:5]=1[CH2:6][O:7][CH2:8][C:9]1[CH:40]=[C:12]2[N:13]=[C:14]([CH3:39])[C:15]([C@H:28]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:16]([N:17]3[CH2:22][CH2:21][C:20]([O:24][CH2:25][CH:26]=C)([CH3:23])[CH2:19][CH2:18]3)[N:11]2[N:10]=1)[CH:2]=C>ClCCCl.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.[Cu]I>[C:35]([O:34][C@@H:28]([C:15]1[C:14]([CH3:39])=[N:13][C:12]2=[CH:40][C:9]3=[N:10][N:11]2[C:16]=1[N:17]1[CH2:22][CH2:21][C:20]([CH3:23])([O:24][CH2:25][CH:26]=[CH:2][CH2:1][C:4]2[CH:44]=[CH:43][CH:42]=[CH:41][C:5]=2[CH2:6][O:7][CH2:8]3)[CH2:19][CH2:18]1)[C:29]([O:31][CH2:32][CH3:33])=[O:30])([CH3:36])([CH3:38])[CH3:37]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of (S)-ethyl 2-(2-(((2-allylbenzyl)oxy)methyl)-7-(4-(allyloxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.059 g, 0.098 mmol) and Copper(I) iodide (0.019 g, 0.098 mmol) in DCE (70.0 ml) was heated to 70° C. Added to this was Hoveyda-Grubbs Catalyst 2nd generation (0.012 g, 19.6 μmol) and the mixture was stirred at 70° C. for two hours then cooled to room temperature overnight. The mixture was concentrated and purified by flash chromatography (Biotage; 0%-50% EtOAc/hexane; 20 CV) to give the title compound (0.0429 g, 0.074 mmol, 76% yield) as a mixture of cis/trans isomers. LCMS (M+H) calcd for C33H45N4O5: 577.33. found: 577.2.

Workup

temperaturethen cooled to room temperature overnight
concentrationThe mixture was concentrated
custompurified by flash chromatography (Biotage; 0%-50% EtOAc/hexane; 20 CV)

Sources & evidence

ORD record: ord-470fa9abbf07474b83d75eb4d934f238
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273067B2

Reaction notes

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