1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67351305, compound

HRID 1672810Notes

Reaction equation

HRID 1672810 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([C:23]4[O:27][C:26](=[O:28])[N:25]([CH2:29][C:30](O)=[O:31])[N:24]=4)[CH:20]=[CH:21][CH:22]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:33]=1.ON1C2C=CC=CC=2N=N1.[CH2:44]([N:46]=[C:47]=NCCCN(C)C)C.CNC.C1COCC1>ClCCl.C(Cl)(Cl)Cl>[CH3:44][N:46]([CH3:47])[C:30](=[O:31])[CH2:29][N:25]1[N:24]=[C:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([N:14]3[CH2:13][C@H:12]4[N:8]([CH2:9][CH2:10][CH2:11]4)[C:7]4[N:33]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][C:6]=4[C:15]3=[O:16])[CH:18]=2)[O:27][C:26]1=[O:28]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 22320367Dimethylamine tetrahydrofuranHCID 67350913HCID 67350913, compound

Product 1

HCID 67351305HCID 67351305, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-2-{5-[3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-2-oxo-1,3,4-oxadiazol-3(2H)-yl}acetic acid (229 mg, 0.49 mmol) obtained in Step 2 was suspended in dichloromethane (5 mL), and the mixture was stirred at room temperature for 2 hours after adding 1-hydroxybenzotriazole (133 mg, 0.98 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (188 mg, 0.98 mmol), and a 2.0 mol/L dimethylamine/THF solution (2.45 mL, 4.88 mmol). After diluting the mixture with chloroform, the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was then purified by silica gel column chromatography to give (S)—N,N-dimethyl 2-{5-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-2-oxo-1,3,4-oxadiazol-3(2H)-yl}acetamide (142 mg, 58%).

Workup

  1. washthe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe residue obtained upon concentration under reduced pressure
  4. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d1a34195375c4568a7cce7ef13aa4940
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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