1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67386157, compound

HRID 1898543Notes

Reaction equation

HRID 1898543 reaction equation
[O:1]([C:8]1[N:9]=[C:10]2[C:16]([C:17](O)=[O:18])=[CH:15][N:14]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:11]2=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)CCCN=C=NCC.[NH2:39][C@H:40]([CH:48]([CH3:50])[CH3:49])[C:41]([N:43]1[CH2:47][CH2:46][CH2:45][CH2:44]1)=[O:42]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:49][CH:48]([CH3:50])[C@@H:40]([NH:39][C:17]([C:16]1[C:10]2[C:11](=[N:12][CH:13]=[C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:9]=2)[N:14]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:26])([CH3:27])[CH3:25])[CH:15]=1)=[O:18])[C:41]([N:43]1[CH2:47][CH2:46][CH2:45][CH2:44]1)=[O:42]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 40459151HCID 40459151, compoundHCID 58522244HCID 58522244, compound

Product 1

HCID 67386157HCID 67386157, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-phenoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.10 g, 0.26 mmol), 4-dimethylaminopyridine (0.048 g, 0.39 mmol) and (3-dimethylamino-propyl)-ethyl-carbodiimide (0.075 g, 0.39 mmol) in CH2Cl2 (2 mL) was added (R)-2-amino-3-methyl-1-pyrrolidin-1-yl-butan-1-one (0.066 g, 0.39 mmol) in CH2Cl2 (0.5 mL). The reaction mixture was stirred at room temperature overnight, then quenched with water and extracted with ethyl acetate (3×). The organic layer was washed with water and saturated aqueous NaCl solution and dried over MgSO4, filtered and concentrated. The residue was purified by SiO2 column chromatography (0-100% EtOAc/hexanes) to afford 2-phenoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-methyl-1-(pyrrolidine-1-carbonyl)-propyl]-amide as a yellow oil.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate (3×)
  3. washThe organic layer was washed with water and saturated aqueous NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by SiO2 column chromatography (0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e8c2b9733817488b930aff2f4b6798ff
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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