Ammonium Chloride → HCID 86708860, compound

HRID 927302Notes

Reaction equation

HRID 927302 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([N:23]3[CH2:28][CH2:27][N:26]([C:29]4[N:34]=[CH:33][CH:32]=[CH:31][N:30]=4)[CH2:25][CH2:24]3)=[O:22])[CH:16]=1)[C:9](=[O:35])[NH:8][C:7]2=[O:36])([O-])=O.[NH4+].[Cl-]>CCO.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([N:23]3[CH2:24][CH2:25][N:26]([C:29]4[N:30]=[CH:31][CH:32]=[CH:33][N:34]=4)[CH2:27][CH2:28]3)=[O:22])[CH:16]=1)[C:9](=[O:35])[NH:8][C:7]2=[O:36]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 68388846HCID 68388846, compound

Product 1

HCID 86708860HCID 86708860, compoundYield 23.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-nitro-1-(3-(4-(pyrimidin-2-yl)piperazine-1-carbonyl)benzyl)-quinazoline-2,4(1H,3H)-dione (50 mg, 0.10 mmol) in EtOH (10 mL) with Fe powder (33.5 mg, 0.60 mmol) and sat. NH4Cl solution (0.2 mL) were refluxed under N2 overnight. The mixture was filtered to remove the solid. The solution was concentrated and purified by flash chromatography (DCM:MeOH=50:3) to give the title compound (10.79 mg, 23.6% yield) as yellow solid. 1H NMR (DMSO-d6): 11.46 (s, 1H), 8.39 (d, J=4.8 Hz, 2H), 7.42-7.31 (m, 4H), 7.20 (d, J=2.7 Hz, 1H), 7.00 (d, J=8.7 Hz, 1H), 6.89 (dd, J=8.7 and 2.7 Hz, 1H), 6.67 (t, J=4.8 Hz, 1H), 5.26 (s, 4H), 3.81-3.68 (m, 8H). MS: m/z 458.3 [M+H]+.

Workup

  1. temperaturewere refluxed under N2 overnight
  2. filtrationThe mixture was filtered
  3. customto remove the solid
  4. concentrationThe solution was concentrated
  5. custompurified by flash chromatography (DCM:MeOH=50:3)

Sources & evidence

ORD record
ord-80761d026a25438e9f12f0ab2633714d
Source dataset
uspto-grants-2016_03
Patent number
US09290460B2

Reaction notes

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