Chloroacetic Acid → HCID 135703296, compound

HRID 2393059Notes

Reaction equation

HRID 2393059 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([O:24][CH3:25])=[O:23])=[CH:12][CH:11]=2)=[C:4]([CH2:26][CH2:27][CH2:28][CH3:29])[N:3]=1.[Cl:30][CH2:31][C:32](O)=[O:33].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH2:26]([C:4]1[N:3]=[C:2]([NH:1][C:32](=[O:33])[CH2:31][Cl:30])[NH:7][C:6](=[O:8])[C:5]=1[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([O:24][CH3:25])=[O:23])=[CH:14][CH:15]=1)[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 135703295HCID 135703295, compound

Product 1

HCID 135703296HCID 135703296, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.4 g of 2-amino-6-butyl-5-[(2'-methoxycarbonylbiphenyl-4-yl)methyl]pyrimidin-4-one in, 10 ml of anhydrous DMF is added in succession with 0.1 g of chloroacetic acid, 0.21 g of DCC and 0.17 g of HOBT. After 8 h under magnetic stirring, the resulting solid is filtered off and the solvent is evaporated under reduced pressure. The residue is taken up with H2O and extracted with AcOEt. The organic phase is dried over Na2 SO4 and evaporated under reduced pressure to obtain 0.47 g of a yellowish spongy solid which can be reacted without further purification.

Workup

  1. filtrationthe resulting solid is filtered off
  2. customthe solvent is evaporated under reduced pressure
  3. extractionextracted with AcOEt
  4. customThe organic phase is dried over Na2 SO4
  5. customevaporated under reduced pressure
  6. customto obtain 0.47 g of a yellowish spongy solid which
  7. customcan be reacted without further purification

Sources & evidence

ORD record
ord-65159a5fa4284778a90863347f21b69a
Source dataset
uspto-grants-1998_09
Patent number
US05804583

Reaction notes

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