Potassium Carbonate → HCID 178523230, compound

HRID 2185196Notes

Reaction equation

HRID 2185196 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:18]=[C:17]([OH:19])[C:16]3[C:11](=[C:12]([C:23](O)=[O:24])[CH:13]=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=3)[N:10]=2)=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(=O)([O-])[O-].[K+].[K+].[NH2:55][CH2:56][CH2:57][C:58]1[CH:59]=[N:60][CH:61]=[CH:62][CH:63]=1>CN(C=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:18]=[C:17]([OH:19])[C:16]3[C:11](=[C:12]([C:23]([NH:55][CH2:56][CH2:57][C:58]4[CH:59]=[N:60][CH:61]=[CH:62][CH:63]=4)=[O:24])[CH:13]=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=3)[N:10]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 8540512-(Pyridin-3-yl)ethan-1-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178524573HCID 178524573, compound

Product 1

HCID 178523230HCID 178523230, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-(4-fluorophenyl)amino-4-hydroxy-6-nitroquinazoline-8-carboxylic acid (41.1 mg), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (23.3 mg), 1-hydroxybenzotriazole hydrate (15.6 mg), and potasium cabonate (16.3 mg) in DMF (2.00 mL) was stirred for 5 minutes and then briefly (15 seconds) heated with a heat gun. The solution was allowed to return to room temperature over 10 minutes of stirring and then 3-(2-aminoethyl)pyridine (17.0 mg) was added. After stirring for an additional 18 hours the resulting mixture was transfered into a centrifuge tube and water (20 mL) was added. A yellow precipitate formed and was the suspension was centrifuged. The aqueous layer was decanted away from the yellow pellet in the bottom of the tube. The yellow pellet was then resuspended in water (20 mL), centrifuged, and decanted two additional times. The resulting yellow pellet was dried in vacuo at 40° C. for 16 h to afford the title compound (35.0 mg). 1H NMR (300 MHz, DMSO-d6 (w/TFA (50 uL,)): 8.97 (d, J=3.0 Hz, 1H), 8.81 (m, 2H), 8.75 (s, 1H), 8.35 (d, J=8.3 Hz, 1H), 7.98 (dd, J=8.1, 5.9 Hz, 1H), 7.50 (dd, J=8.9, 5.0 Hz, 2H), 7.32 (t, J=8.7 Hz, 2H), 3.50 (m, 2H), 2.84 (m, 2H). HPLC (Method G): 1.59 min. MS (APCI+): m/z 449.

Workup

  1. temperaturebriefly (15 seconds) heated with a heat gun
  2. waitto return to room temperature over 10 minutes
  3. stirringof stirring
  4. stirringAfter stirring for an additional 18 hours the resulting mixture
  5. customwas transfered into a centrifuge tube
  6. customA yellow precipitate formed
  7. customThe aqueous layer was decanted away from the yellow pellet in the bottom of the tube
  8. customcentrifuged, and decanted two additional times
  9. customThe resulting yellow pellet was dried in vacuo at 40° C. for 16 h

Sources & evidence

ORD record
ord-c6a4bd0037e149dea478d5eb93dcdda0
Source dataset
uspto-grants-2002_06
Patent number
US06399603B1

Reaction notes

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