1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59753760, compound

HRID 751735Notes

Reaction equation

HRID 751735 reaction equation
[ClH:1].[CH2:2]([O:4][C:5](=[O:16])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[NH2:7])[CH3:3].CC[N:19]([CH:23]([CH3:25])C)[CH:20]([CH3:22])[CH3:21].C1C=CC2N([OH:35])N=NC=2C=1.CCN=C=[N:40][CH2:41][CH2:42][CH2:43]N(C)C>CN(C=O)C>[CH2:2]([O:4][C:5](=[O:16])[C@@H:6]([NH:7][C:22]([C:20]1[NH:19][C:23]2=[N:40][C:41]([Cl:1])=[CH:42][CH:43]=[C:25]2[CH:21]=1)=[O:35])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=1)[CH3:3]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 56777149H-P-FLUORO-PHE-OET HCL

Product 1

HCID 59753760HCID 59753760, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-chloro-1H-pyrrolo[2,3b]pyridine-2-carboxylic acid (Preparation 110, 450 mg, 2.29 mmol) in DMF (20 mL) was added 4-fluoro phenylalanine ethyl ester hydrochloride (624 mg, 2.52 mmol), DIPEA (1.40 mL, 8.01 mmol) and HOBt. (386 mg, 2.52 mmol) and the reaction stirred. After 5 min EDCI (570 mg, 2.98 mmol) was added and stirring continued for 16 hr. Solvent was removed in vacuo then crude material partitioned between ethyl acetate (75 mL) and water (50 mL). Organics were washed with NaHCO3 solution (3×50 mL) then brine (2×50 mL), dried (MgSO4) and THE solvent removed in vacuo to give the title compound. m/z (ES+)=389.90 [M+H]+; RT=3.79 min.

Workup

  1. stirringstirring
  2. customSolvent was removed in vacuo
  3. customcrude material partitioned between ethyl acetate (75 mL) and water (50 mL)
  4. washOrganics were washed with NaHCO3 solution (3×50 mL)
  5. dry with materialbrine (2×50 mL), dried (MgSO4)
  6. customTHE solvent removed in vacuo

Sources & evidence

ORD record
ord-5bf2b87d15544a619ac4358eda8bd4b0
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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