2,6-Lutidine → HCID 58382263, compound

HRID 1628011Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][C:5]([NH:7][CH2:8][C:9]1[N:10]=[C:11]2[CH:17]=[C:16]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=4)[N:20]([CH3:29])[CH:19]=3)[N:15]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:12]2=[N:13][CH:14]=1)=[O:6].N1C(C)=CC=CC=1C.[Si:46](OS(C(F)(F)F)(=O)=O)([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47]>C(Cl)Cl>[Si:46]([O:1][CH2:2][CH2:3][CH2:4][C:5]([NH:7][CH2:8][C:9]1[N:10]=[C:11]2[CH:17]=[C:16]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=4)[N:20]([CH3:29])[CH:19]=3)[N:15]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:35])[CH3:36])[C:12]2=[N:13][CH:14]=1)=[O:6])([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47]

Participants

Conditions

Temperature: -5 °C

Procedure

A flask was charged with 4-hydroxy-N-((6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)butanamide (0.130 g, 0.248 mmol) and DCM (5 mL). The mixture was cooled to about −5° C. To the mixture was added 2,6-lutidine (0.064 mL, 0.54 mmol). After about 2 min, TBDMSOTf (0.063 mL, 0.273 mmol) was added. The mixture was stirred at about −5 to 0° C. for about 2 h. The mixture was concentrated under reduced pressure and the residue was purified using silica gel chromatography with an elution gradient of 0 to 80% EtOAc/heptane to give 4-(tert-butyldimethylsilyloxy)-N-((6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)butanamide (0.117 g, 74%): LC/MS (Table 2, Method a) Rt=3.40 min; MS m/z 638 (M+H)+.

Workup

concentrationThe mixture was concentrated under reduced pressure
customthe residue was purified

Sources & evidence

ORD record: ord-37db9eb744574becbd330539cd01af7b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785639B2

Reaction notes

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