Diisopropylethylamine → HCID 11584219, compound

HRID 1611098Notes

Reaction equation

HRID 1611098 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[N:13][C:14]([SH:17])=[N:15][CH:16]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH2:28][CH:27]([CH2:31][NH:32][C:33](=[O:36])[CH2:34]Cl)[CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH2:28][CH:27]([CH2:31][NH:32][C:33](=[O:36])[CH2:34][S:17][C:14]2[N:13]=[CH:12][C:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:16][N:15]=2)[CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 66564636HCID 66564636, compoundHCID 178488772HCID 178488772, compound

Product 1

HCID 11584219HCID 11584219, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(3,4-Dimethoxy-phenyl)-pyrimidine-2-thiol 1f (0.75 g, 3 mmol) was added to a solution of the 2-chloroacetamide 1d (1.3 g, ˜80% purity, ˜3.6 mmol, obtained from step 3) and diisopropylethylamine (0.78 mL, 4.5 mmol, 1.5 equiv) in dry CH2Cl2. The resulting suspension was stirred at rt for about 2 h, at which time the reaction mixture became a dark brown solution and all the solid disappeared. The mixture was then concentrated and chromatographed on silica gel (ethyl acetate). The fractions containing the major product were combined and concentrated to an oily residue. Trituration of the oil with ether afforded 3-({2-[5-(3,4-dimethoxy-phenyl)-pyrimidin-2-ylsulfanyl]-acetylamino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester 1g (0.83 g, 55%) as a dark brown solid.

Workup

  1. concentrationThe mixture was then concentrated
  2. customchromatographed on silica gel (ethyl acetate)
  3. additionThe fractions containing the major product
  4. concentrationconcentrated to an oily residue

Sources & evidence

ORD record
ord-33c1b6adbec54fcc9a0c77e5bbadb192
Source dataset
uspto-grants-2006_01
Patent number
US06984643B2

Reaction notes

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