Diethyl Ether → HCID 66762548, compound

HRID 474394Notes

Reaction equation

HRID 474394 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:32]=[CH:31][C:15]([CH2:16][NH:17][C:18]2[C:27]3[C:22](=[C:23]([C:28]([NH2:30])=[O:29])[CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20][N:19]=2)=[CH:14][CH:13]=1.C(N(CC)CC)C.CCOCC>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:16][NH:17][C:18]3[C:27]4[C:22](=[C:23]([C:28]([NH2:30])=[O:29])[CH:24]=[CH:25][CH:26]=4)[N:21]=[CH:20][N:19]=3)=[CH:31][CH:32]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 66763600HCID 66763600, compound

Product 1

HCID 66762548HCID 66762548, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-fluorobenzoyl chloride (220 μL, 0.5 M in anhydrous DCM, 0.10 mmol, 1.1 equiv.) was added to a solution of 4-[(4-aminobenzyl)amino]quinazoline-8-carboxamide (30 mg, 0.09 mmol, 1.0 equiv.) and triethylamine (38 μL, 0.27 mmol, 3.0 equiv.) in anhydrous DCM (2 mL). The resulting mixture was stirred at rt overnight. Ether (2 mL) was added. The precipitate was filtered, washed with ether and DCM to yield the title compound in 72% yield. Mass: M+H+: 416.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with ether and DCM

Sources & evidence

ORD record
ord-f7aceb4912584f0589d5ba32c91151dc
Source dataset
uspto-grants-2014_01
Patent number
US08637532B2

Reaction notes

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