Oxalyl chloride → 4-(2-Fluorophenyl)-6-methyl-2-morpholin-4-yl-pyrimidine-5-carboxylic acid benzyl-isopropyl-amide

HRID 883015Notes

Reaction equation

HRID 883015 reaction equation
C(Cl)(=O)C(Cl)=O.[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[C:19]([C:20](O)=[O:21])=[C:18]([CH3:23])[N:17]=[C:16]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:15]=1.[CH2:30]([NH:37][CH:38]([CH3:40])[CH3:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C=O)C>[CH2:30]([N:37]([CH:38]([CH3:40])[CH3:39])[C:20]([C:19]1[C:14]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[F:7])=[N:15][C:16]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)=[N:17][C:18]=1[CH3:23])=[O:21])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 66024IsopropylbenzylamineHCID 81531DiisopropylethylamineHCID 594211804-(2-Fluorophenyl)-6-methyl-2-morpholin-4-yl-pyrimidine-5-carboxylic acid

Product 1

HCID 116047934-(2-Fluorophenyl)-6-methyl-2-morpholin-4-yl-pyrimidine-5-carboxylic acid benzyl-isopropyl-amideYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of 2 M oxalyl chloride in CH2Cl2 (0.070 mL, 0.14 mmol) was added to a stirred solution of 4-(2-fluorophenyl)-6-methyl-2-morpholin-4-yl-pyrimidine-5-carboxylic acid (0.03 g, 0.09 mmol) in CH2Cl2 (2 mL) and DMF (0.030 mL) at room temperature, and stirring continued for 15 min. A solution of N-benzylisopropylamine (0.013 g, 0.1 mmol) in CH2Cl2 (1 mL) and diisopropylethylamine (0.044 mL, 0.25 mmol) were added and stirred for 24 hr. The solvent was removed under reduced pressure, and the residue was purified by Biotage SP1 on packed silica gel column (10%-80% EtOAc/Hexanes gradient) to give 4-(2-fluorophenyl)-6-methyl-2-morpholin-4-yl-pyrimidine-5-carboxylic acid benzyl-isopropyl-amide (0.016 g, 40%). Mass Spec. LCMS 449 (M+1).

Workup

  1. stirringstirred for 24 hr
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by Biotage SP1

Sources & evidence

ORD record
ord-0be2ca42cef94787856874bc481bcee1
Source dataset
uspto-grants-2012_08
Patent number
US08236815B2

Reaction notes

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