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Triethylamine → 1-chloro-9-(1-methyl-1H-pyrazol-4-yl)-N-(1,3-thiazol-2-ylmethyl)benzo[c]-1,6-naphthyridin-6-amine

HRID 2192968
Notes
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Reaction equation

HRID 2192968 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.Cl.[NH2:24][CH2:25][C:26]1[S:27][CH:28]=[CH:29][N:30]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CC(N(C)C)=O>[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:24][CH2:25][C:26]1[S:27][CH:28]=[CH:29][N:30]=1)=[N:7]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 42614216(1,3-Thiazol-2-yl)methanamine hydrochlorideHCID 593755141,6-dichloro-9-(1-methyl-1H-pyrazol-4-yl)benzo[c]-1,6-naphthyridine

Product 1

HCID 593754881-chloro-9-(1-methyl-1H-pyrazol-4-yl)-N-(1,3-thiazol-2-ylmethyl)benzo[c]-1,6-naphthyridin-6-amine

Reagents, catalysts & solvents

1
HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °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 2-aminomethylthiazole hydrochloride (92 mg, 0.608 mmol) in DMA (1.5 mL), triethylamine (85 μl, 0.608 mmol) was added. The reaction mixture was heated to 130° C. for 1 h via microwave irradiation. After cooling to room temperature, aqueous sodium hydrogen carbonate (saturated) was added. The aqueous layer 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-(1,3-thiazol-2-ylmethyl)benzo[c]-1,6-naphthyridin-6-amine as a yellow solid. LRMS (APCI) calc'd for (C20H16ClN6S) [M+H]+, 407.1; found 407.0.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous layer 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-7681b29b0a404f63b86d019ddb1ea459
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