2-Naphthoic acid → HCID 59514514, compound

HRID 1159657Notes

Reaction equation

HRID 1159657 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:7]2[N:12]=[C:11]([Cl:13])[C:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:9]([Cl:19])[N:8]=2)=[CH:4][CH:3]=1.[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[C:32](O)=[O:33].CCOC(C)=O>C1COCC1>[Cl:19][C:9]1[C:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:11]([Cl:13])[N:12]=[C:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:32]([C:23]3[CH:24]=[CH:25][C:26]4[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:22]=3)=[O:33])=[CH:21][CH:20]=2)[N:8]=1

Participants

5

Reactant 3

HCID 71232-Naphthoic acidHCID 8857Ethyl AcetateHCID 59514483HCID 59514483, compound

Product 1

HCID 59514514HCID 59514514, compoundYield 669.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl [2-(4-aminobenzyl)-4,6-dichloropyrimidin-5-yl]acetate (0.073 g, 0.23 mmol), 2-naphthoic acid (0.048 g, 0.028 mmol), and WSCI (0.049 g, 0.026 mmol) in anhydrous THF (3 mL) was stirred at room temperature under Ar atmosphere for 10 hours. EtOAc (80 mL) was then introduced and the organic phase was washed sequentially with saturated NaHCO3, water, and brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product thus obtained as a light orange oil was triturated with diisopropyl ether and the separated solids was collected by suction to give methyl {4,6-dichloro-2-[4-(2-naphthoylamino)benzyl]pyrimidin-5-yl}acetate (0.090 g, 78% yield) as a white powder.

Workup

  1. washthe organic phase was washed sequentially with saturated NaHCO3, water, and brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product thus obtained as a light orange oil
  6. customwas triturated with diisopropyl ether
  7. customthe separated solids was collected by suction

Sources & evidence

ORD record
ord-eecc3af786a74729baf0f4b42dfe0662
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

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