Tetrafluoroborate → HCID 86712345, compound

HRID 592482Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:14]=[N:15][N:16]([CH3:18])[CH:17]=2)[N:3]=1.[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1([C:30]([NH2:32])=[O:31])[CH2:29][CH2:28]1)#[CH:20].F[B-](F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:18][N:16]1[CH:17]=[C:13]([NH:12][C:4]2[N:3]=[C:2]([C:20]#[C:19][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3([C:30]([NH2:32])=[O:31])[CH2:29][CH2:28]3)[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=2)[CH:14]=[N:15]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a degassed mixture of 4-chloro-N-(1-methyl-1H-pyrazol-4-yl)-5-(trifluoromethyl)pyrimidin-2-amine A74 (0.178 g, 0.640 mmol), 1-(2-ethynylphenyl)cyclopropanecarboxamide K6 (0.172 g, 0.928 mmol), PdCl2(PPh3)2 (0.005 g, 0.007 mmol), t-Bu3PH.BF4 (0.005 g, 0.02 mmol) and copper(I) iodide (0.003 g, 0.02 mmol) in DMF (8.0 mL) was added DIPEA (0.33 mL, 1.9 mmol). The mixture was heated in the microwave for 2×20 minutes at 100° C. before being concentrated under reduced pressure. Purification by silica gel column chromatography (Isolera, 0-100% EtOAc petroleum benzine 40-60° C. then 0-20% MeOH in EtOAc) gave the title compound A75 (0.120 g, 44%). LCMS-D: rt 3.30 min; m/z 427.2 [M+H]+.

Workup

concentrationbefore being concentrated under reduced pressure
customPurification by silica gel column chromatography (Isolera, 0-100% EtOAc petroleum benzine 40-60° C.

Sources & evidence

ORD record: ord-a2ecf98f18cf4176baf55c36d3169af9
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238644B2

Reaction notes

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