Potassium Carbonate → HCID 178520493, compound

HRID 2185193Notes

Reaction equation

HRID 2185193 reaction equation
Cl.CN(C)[CH2:4][CH2:5][CH2:6][N:7]=C=NCC.ON1C2N=CC=CC=2N=N1.C(=O)([O-])[O-].[K+].[K+].[Cl:29][C:30]1C=CC(CN)=[CH:32][CH:31]=1.[Cl:38][C:39]1[CH:40]=[C:41]([NH:46][C:47]2[N:56]=[C:55]([OH:57])[C:54]3[C:49](=[C:50]([CH2:61][CH2:62][C:63]([OH:65])=O)[CH:51]=[C:52]([N+:58]([O-:60])=[O:59])[CH:53]=3)[N:48]=2)[CH:42]=[CH:43][C:44]=1[Cl:45]>CN(C)C=O>[Cl:29][C:30]1[CH:4]=[CH:5][C:6]([NH:7][C:63](=[O:65])[CH2:62][CH2:61][C:50]2[CH:51]=[C:52]([N+:58]([O-:60])=[O:59])[CH:53]=[C:54]3[C:49]=2[N:48]=[C:47]([NH:46][C:41]2[CH:42]=[CH:43][C:44]([Cl:45])=[C:39]([Cl:38])[CH:40]=2)[N:56]=[C:55]3[OH:57])=[CH:32][CH:31]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 660364-ChlorobenzylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178525334HCID 178525334, compound

Product 1

HCID 178520493HCID 178520493, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.023 g), 1-hydroxy-7-azabenzotriazole (0.016 g) and potassium carbonate (0.016 g) in 2 mL of dry N,N-dimethylformamide was added 4-chlorobenzylamine (0.015 mL), followed 3-[2-(3,4-Dichlorophenylamino)-4-hydroxy-6-nitro-quinazolin-8-yl]-propionic acid (0.050 g). The resulting suspension was stirred at room temperature for 28 h, then was quenched with 4 mL of water. The precipitate which formed was isolated by filtration, washed with water and dried to afford the title compound as an orange solid (0.035 g). 1H NMR (300 MHz, DMSO-d6): 10.26 (s, 1H), 8.59 (d, J=2.6 Hz, 1H), 8.39 (d, J=2.6 Hz, 1H), 8.35-8.31 (m, 1H), 8.16 (d, J=2.8 Hz, 1H), 7.76 (dd, J=8.8, 2.8 Hz, 1H), 7.50 (d, J=8.8 Hz, 1H), 7.24 (d, J=8.5 Hz, 1H), 7.10 (d, J=6.9 Hz, 2H), 4.20 (d, J=6.1 Hz, 2H), 3.20 (t, J=6.9 Hz, 2H), 2.63 (t, J=7.1 Hz, 2H). HPLC (Method J2): 4.6 min; MS (ES−): m/z 544/546.

Workup

  1. customwas quenched with 4 mL of water
  2. customThe precipitate which formed
  3. customwas isolated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-64b0718466164ec8970b6e8c2e4cb58d
Source dataset
uspto-grants-2002_06
Patent number
US06399603B1

Reaction notes

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