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Sodium Carbonate → 3-[6-isopropyl-9-(1-methyl-1H-pyrazol-4-yl)-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl]prop-2-ynamide

HRID 2193023
Notes
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Reaction equation

HRID 2193023 reaction equation
Br[C:2]1[CH:24]=[CH:23][C:5]2[C:6]([CH:20]([CH3:22])[CH3:21])=[N:7][C:8]3[C:9]([C:15]#[C:16][C:17]([NH2:19])=[O:18])=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1.[CH3:25][N:26]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[N:27]1.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd]Cl.CN(C=O)C>[CH:20]([C:6]1[C:5]2[CH:23]=[CH:24][C:2]([C:29]3[CH:28]=[N:27][N:26]([CH3:25])[CH:30]=3)=[CH:3][C:4]=2[C:13]2[C:12](=[O:14])[NH:11][CH:10]=[C:9]([C:15]#[C:16][C:17]([NH2:19])=[O:18])[C:8]=2[N:7]=1)([CH3:21])[CH3:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 593756833-(9-Bromo-6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl)prop-2-ynamideHCID 86761722dppp CH2Cl2

Product 1

HCID 593753663-[6-isopropyl-9-(1-methyl-1H-pyrazol-4-yl)-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl]prop-2-ynamide

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3-(9-bromo-6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl)prop-2-ynamide (57 mg, 0.15 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (62 mg, 0.30 mmol), and PdCl2(dppp-CH2Cl2 adduct (24 mg, 0.030 mmol) were added to a vial, followed by DMF (1.8 ml) and aqueous sodium carbonate (2M) (0.15 ml, 0.30 mmol). The resulting suspension was purged with argon (subsurface bubbling) for 10 min, then heated in a microwave reactor at 100° C. for 30 min. The mixture was cooled, diluted with DMF, and filtered to remove salts. The solution was purified directly by preparative reverse phase HPLC eluting with an acetonitrile/water (with 0.05% TFA as a modifier) gradient, to afford 3-[6-isopropyl-9-(1-methyl-1H-pyrazol-4-yl)-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl]prop-2-ynamide. 1H NMR (500 MHz, DMSO-D6) δ 12.15 (br s, 1H), 10.15 (s, 1H), 8.46 (d, 1H), 8.34 (s, 1H), 8.01-7.98 (overlapping m, 3H), 7.89 (br s, 1H), 7.56 (br s, 1H), 4.08 (septet, 1H), 3.92 (s, 3H), 1.41 (d, 6H). LRMS (ESI) calc'd for (C22H19N5O2) [M+H]+, 386.2; found 386.1.

Workup

  1. customThe resulting suspension was purged with argon (subsurface bubbling) for 10 min
  2. temperatureThe mixture was cooled
  3. additiondiluted with DMF
  4. filtrationfiltered
  5. customto remove salts
  6. customThe solution was purified directly by preparative reverse phase HPLC
  7. washeluting with an acetonitrile/water (with 0.05% TFA as a modifier) gradient

Sources & evidence

ORD record
ord-833670c25b884cabbb056b97224ad00d
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08329722B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes