Triethylamine → HCID 67175746, compound

HRID 1027503Notes

Reaction equation

HRID 1027503 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][C:7]2[N:8]=[C:9]([O:29][CH2:30][CH2:31][CH3:32])[C:10]3[N:15]=[C:14]([C:16]4[CH:26]=[C:25]([CH3:27])[C:19]([O:20][CH2:21][C:22](Cl)=[O:23])=[C:18]([CH3:28])[CH:17]=4)[O:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.Cl.[C:36]([O:40][C:41](=[O:44])[CH2:42][NH2:43])([CH3:39])([CH3:38])[CH3:37].C(N(CC)CC)C>ClCCl>[C:36]([O:40][C:41](=[O:44])[CH2:42][NH:43][C:22](=[O:23])[CH2:21][O:20][C:19]1[C:18]([CH3:28])=[CH:17][C:16]([C:14]2[O:13][C:11]3[N:12]=[C:7]([CH2:6][C:5]4[CH:33]=[CH:34][C:2]([Cl:1])=[CH:3][CH:4]=4)[N:8]=[C:9]([O:29][CH2:30][CH2:31][CH3:32])[C:10]=3[N:15]=2)=[CH:26][C:25]=1[CH3:27])([CH3:39])([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 86656418HCID 86656418, compound

Product 1

HCID 67175746HCID 67175746, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

200 mg of {4-[5-(4-chloro-benzyl)-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethyl-phenoxy}-acetyl chloride were dissolved in 2 ml of dichloromethane, and the solution was slowly added to a solution of 67 mg of glycine tert-butyl ester hydrochloride and 121 mg of triethylamine in 3 ml of dichloromethane. The mixture was stirred for 18 h at room temperature. Then the solvent was distilled off in vacuo and the product was isolated via preparative HPLC (method HPLC2) to yield 53 mg of the title compound.

Workup

  1. distillationThen the solvent was distilled off in vacuo
  2. customthe product was isolated via preparative HPLC (method HPLC2)

Sources & evidence

ORD record
ord-221a36895b6d4e4cb6b672408fc0f08c
Source dataset
uspto-grants-2014_05
Patent number
US08735387B2

Reaction notes

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