Triethylamine → HCID 57954393, compound

HRID 221379Notes

Reaction equation

HRID 221379 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][CH2:8][C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([C:20]#[N:21])[CH:15]=3)[O:11][N:10]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:29]1([O:35][C:36](Cl)=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl.CCOC(C)=O>[C:29]1([O:35][C:36]([N:1]2[CH2:6][CH2:5][CH:4]([O:7][CH2:8][C:9]3[N:13]=[C:12]([C:14]4[CH:19]=[CH:18][N:17]=[C:16]([C:20]#[N:21])[CH:15]=4)[O:11][N:10]=3)[CH2:3][CH2:2]2)=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 57954436HCID 57954436, compound

Product 1

HCID 57954393HCID 57954393, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-[3-(piperidin-4-yloxymethyl)[1,2,4]oxadiazol-5-yl]pyridine-2-carbonitrile (Preparation 25, 700 mg, 2.5 mmol) in DCM (30 ml) was added triethylamine (0.7 ml, 4.9 mmol). The resulting solution was transferred to a stirred solution of phenylchloroformate (0.62 ml, 4.9 mmol) in DCM (30 ml) and stirring was continued for 30 min at rt. The reaction mixture was diluted with EtOAc (250 ml) then washed successively with water (100 mL), saturated aqueous sodium carbonate (100 ml) and brine (100 ml). The organics were dried (MgSO4) then adsorbed onto silica gel. Purification via chromatography (EtOAc-IH, 1:1 to 3:2) afforded the title compound: RT=3.63 nm in; m/z (ES+)=406.01 [M+H]+.

Workup

  1. washthen washed successively with water (100 mL), saturated aqueous sodium carbonate (100 ml) and brine (100 ml)
  2. dry with materialThe organics were dried (MgSO4)
  3. customPurification via chromatography (EtOAc-IH, 1:1 to 3:2)

Sources & evidence

ORD record
ord-e8eca62c307b48de838e2ccd657e7b3b
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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