Potassium Carbonate → HCID 68007725, compound

HRID 526921Notes

Reaction equation

Br[CH2:2][C@H:3]([CH3:6])[CH2:4][OH:5].[Cl:7][C:8]1[CH:9]=[C:10]2[C:16]([C:17]3[N:22]=[C:21]([NH:23][CH2:24][C@@H:25]4[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]4)[C:20]([F:31])=[CH:19][N:18]=3)=[CH:15][NH:14][C:11]2=[N:12][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[Cl:7][C:8]1[CH:9]=[C:10]2[C:16]([C:17]3[N:22]=[C:21]([NH:23][CH2:24][C@@H:25]4[CH2:30][CH2:29][CH2:28][N:27]([CH2:2][C@H:3]([CH3:6])[CH2:4][OH:5])[CH2:26]4)[C:20]([F:31])=[CH:19][N:18]=3)=[CH:15][NH:14][C:11]2=[N:12][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (R)-3-bromo-2-methylpropan-1-ol (0.006 mL, 0.055 mmol) and (R)-2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-(piperidin-3-ylmethyl)-pyrimidin-4-amine, 12a, (0.020 g, 0.055 mmol) in CH3CN (2 mL) was added K2CO3 (0.023 g, 0.165 mmol). The reaction mixture was heated at 80° C. at for 24 h. The solvent was concentrated under reduced pressure and the resulting residue was purified by preparatory HPLC (0.1% TFA-H2O/acetonitrile) to afford the desired product, 135.

Workup

concentrationThe solvent was concentrated under reduced pressure
customthe resulting residue was purified by preparatory HPLC (0.1% TFA-H2O/acetonitrile)

Sources & evidence

ORD record: ord-03e2cd5a83d540a3a09bce9778ac269f
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345708B2

Reaction notes

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