4-Morpholinecarbonyl chloride → HCID 11684718, compound

HRID 1693502Notes

Reaction equation

HRID 1693502 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][NH:17][C:11]=3[N:10]=[C:9]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[CH:4][CH:3]=1.[N:25]1([C:31](Cl)=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:31]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[O:32])[C:11]=3[N:10]=[C:9]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 848104-Morpholinecarbonyl chlorideHCID 57897824HCID 57897824, compound

Product 1

HCID 11684718HCID 11684718, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-(4-bromo-phenyl)-6-(2-fluoro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (20.0 mg, 0.052 mmol) in anhydrous pyridine (0.5 mL) is added 4-morpholinecarbonyl chloride (7.27 μL, 0.062 mmol). The mixture is stirred at room temperature for 2 h before removal of the solvent. The residue is purified by preparative LCMS followed by preparative TLC to provide the title compound (9.1 mg, 35% yield) as a white solid product; 1H NMR (CDCl3, 400 MHz) δ 8.91 (s, 1H), 7.42-7.28 (m, 4H), 7.11 (t, 1H), 7.02 (d, 2H), 6.88 (t, 1H), 4.15-3.84 (m, 8H); HPLC-MS calculated for C22H17BrFN5O3 (M+H+) 498.0. Found: 498.0.

Workup

  1. customThe residue is purified by preparative LCMS

Sources & evidence

ORD record
ord-f29e872ea846499887d723b88aa321f4
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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