N-Aminomorpholine → HCID 25099733, compound

HRID 2381959Notes

Reaction equation

HRID 2381959 reaction equation
[C:1]([C:9]1[N:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11][N:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[N:24]1([NH2:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[N:24]1([NH:30][C:15]([C:12]2[CH:13]=[N:14][C:9]([C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[N:10][CH:11]=2)=[O:17])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 20315N-AminomorpholineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 68556656HCID 68556656, compound

Product 1

HCID 25099733HCID 25099733, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

2-Benzoyl-pyrimidine-5-carboxylic acid (50 mg, 0.22 mmol) is dissolved in anhydrous DCM (5 mL), and a 2 M oxalyl chloride (0.26 mmol, 0.13 mL) solution in DCM is added at rt followed by one drop of DMF. The mixture is stirred at rt for 2 h, and then concentrated in vacuo. The residue is dissolved in DCM (5 mL), and morpholine-4-ylamine (0.24 mmol, 25 mg) is added, followed by DIPEA (0.44 mmol, 57 mg). The reaction mixture is stirred at rt overnight, and then concentrated in vacuo. The residue is purified by silica gel column chromatography eluting with 10% MeOH in DCM to afford 2-benzoyl-pyrimidine-5-carboxylic acid morpholin-4-ylamide (42 mg) as a solid. MS: 313 (M+H). IC50=342 nM.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in DCM (5 mL)
  3. stirringThe reaction mixture is stirred at rt overnight
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by silica gel column chromatography
  6. washeluting with 10% MeOH in DCM

Sources & evidence

ORD record
ord-e1a529365e3242e7863519645995d3ef
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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