4-Chlorobenzoic Acid → HCID 59514566, compound

HRID 2422152Notes

Reaction equation

HRID 2422152 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([N:13]([CH3:15])[CH3:14])[N:5]=[C:4]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][CH3:24])=[CH:19][CH:18]=2)[N:3]=1.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[Cl:42][C:43]1[CH:51]=[CH:50][C:46]([C:47](O)=[O:48])=[CH:45][CH:44]=1>CCOC(C)=O>[CH3:12][O:11][C:9](=[O:10])[CH2:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]([C:47](=[O:48])[C:46]3[CH:50]=[CH:51][C:43]([Cl:42])=[CH:44][CH:45]=3)[CH3:24])=[CH:19][CH:18]=2)=[N:5][C:6]=1[N:13]([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 63184-Chlorobenzoic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 59514507HCID 59514507, compound

Product 1

HCID 59514566HCID 59514566, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl {4-chloro-6-(dimethylamino)-2-[4-(methylamino)benzyl]pyrimidin-5-yl}acetate (0.080 g, 0.23 mmol), 1-hydroxybenzotriazole (0.043 g, 0.32 mmol), triethylamine (0.11 mL, 0.80 mmol), and 4-chlorobenzoic acid (0.043 g, 0.28 mmol) was treated with WSCI (0.066 g, 0.34 mmol) at room temperature and the reaction mixture was stirred at room temperature for 16 hours. EtOAc was then added and the organic layer was washed sequentially with 0.5N HCl, saturated NaHCO3, and brine, dried over anhydrous Na2SO4, filtered, and concentrated to dryness to give the crude product methyl[4-chloro-2-{4-[(4-chlorobenzoyl)(methyl)amino]benzyl}-6-(dimethylamino)pyrimidin-5-yl]acetate.

Workup

  1. washthe organic layer was washed sequentially with 0.5N HCl, saturated NaHCO3, and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-87638c72fb6d4d24a43fe21e6c38926e
Source dataset
uspto-grants-2011_06
Patent number
US07960393B2

Reaction notes

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