Acetic Acid → HCID 86677564, compound

HRID 2401107Notes

Reaction equation

HRID 2401107 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:19][CH:20]=O)[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[NH2:22][C:23]1[CH:24]=[N:25][C:26]([Cl:29])=[N:27][CH:28]=1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH4+].[OH-]>ClCCCl.O>[CH2:1]([O:3][C:4]([C:6]1([CH2:19][CH2:20][NH:22][C:23]2[CH:24]=[N:25][C:26]([Cl:29])=[N:27][CH:28]=2)[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 14923Ammonium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 122159932-Chloropyrimidin-5-amineHCID 584784234-(2-Oxoethyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

Product 1

HCID 86677564HCID 86677564, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a mixture of 4-(2-oxo-ethyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (324 mg, 1.08 mmol) and 5-amino-2-chloropyrimidine (140 mg, 1.08 mmol) in DCE (3 mL) was added AcOH (0.19 mL, 3.4 mmol) followed by NaBH(OAc)3 (687 mg, 3.24 mmol) and then stirred for 18 hours at ambient temperature. Water was added and the solution was brought to pH 9 with NH4OH. The two layers were separated and the aqueous was extracted with CH2Cl2, dried over Na2SO4, filtered and concentrated to afford a solid which was purified by flash column chromatography (5 to 50% EtOAc/Heptane) to provide 188 mg (42% yield) of the title compound.

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous was extracted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a solid which
  7. customwas purified by flash column chromatography (5 to 50% EtOAc/Heptane)

Sources & evidence

ORD record
ord-cc6dc3f1af10480d9201161615a27c29
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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