1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178513657, compound

HRID 2359987Notes

Reaction equation

HRID 2359987 reaction equation
[C:1]1([C:7]2[N:8]([C:19]3[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=3)[C:9]([CH2:12][CH2:13][C:14]3[NH:18][N:17]=[N:16][N:15]=3)=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC[N:30]=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:1]1([C:7]2[N:8]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([NH2:30])=[O:24])=[CH:21][CH:20]=3)[C:9]([CH2:12][CH2:13][C:14]3[NH:18][N:17]=[N:16][N:15]=3)=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 1785244444-{2-phenyl-5-[2-(1H-tetrazol-5-yl)-ethyl]-pyrrol-1-yl}-benzoic acid

Product 1

HCID 178513657HCID 178513657, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-{2-phenyl-5-[2-(1h-tetrazol-5-yl)-ethyl]-pyrrol-1-yl}-benzoic acid (0.37 mmol, 1.0 eq.) in DMF (10 ml) were added EDCI (1.48 mmol, 4.0 eq), HOBt hydrate (1.48 mmol, 4.0 eq.), and DIEA (diisopropylethylamine, 2.96 mmol, 8.0 eq.). The resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with DCM (75 mL) and 10% citric acid (50 mL). The organic layer was washed with saturated NaHCO3 (75 mL). The saturated NaHCO3 was acidified with 1M HCl and extracted with DCM (2×100 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo. The crude material was purified by prep HPLC to give product as a white solid, 30% yield.

Workup

  1. washThe organic layer was washed with saturated NaHCO3 (75 mL)
  2. extractionextracted with DCM (2×100 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe crude material was purified by prep HPLC
  6. customto give product as a white solid, 30% yield

Sources & evidence

ORD record
ord-cb835a92fcb74135b99e8feb91eb7227
Source dataset
uspto-grants-2014_04
Patent number
US08686015B2

Reaction notes

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