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3-Aminopyridine → 1-chloro-9-(1-methyl-1H-pyrazol-4-yl)-N-pyridin-3-ylbenzo[c]-1,6-naphthyridin-6-amine

HRID 2192967
Notes
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Reaction equation

HRID 2192967 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([C:17]3[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=3)[CH:14]=[CH:13][C:5]=1[C:6](Cl)=[N:7]2.[NH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1.CC(C)([O-])C.[Na+].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([C:17]3[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=3)[CH:14]=[CH:13][C:5]=1[C:6]([NH:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[N:7]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 100093-AminopyridineHCID 25517Ammonium ChlorideHCID 23676156Sodium t-butoxideHCID 593755141,6-dichloro-9-(1-methyl-1H-pyrazol-4-yl)benzo[c]-1,6-naphthyridine

Product 1

HCID 593755971-chloro-9-(1-methyl-1H-pyrazol-4-yl)-N-pyridin-3-ylbenzo[c]-1,6-naphthyridin-6-amine

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 1,6-dichloro-9-(1-methyl-1H-pyrazol-4-yl)benzo[c]-1,6-naphthyridine (50 mg, 0.152 mmol) and 3-aminopyridine (14.30 mg, 0.152 mmol) in THF (1.5 mL), sodium tert-butoxide (43.8 mg, 0.456 mmol) was added. The reaction mixture was heated to 85° C. for 1 h. After cooling to room temperature, aqueous ammonium chloride (saturated) and ethyl acetate were added. The mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure to afford 1-chloro-9-(1-methyl-1H-pyrazol-4-yl)-N-pyridin-3-ylbenzo[c]-1,6-naphthyridin-6-amine as a yellow solid. LRMS (APCI) calc'd for (C21H15ClN6) [M+H]+, 387.1; found 387.1.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a22ab14a53d7405c8e25948fdc688ff7
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