1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-benzyl-2-(S)-hydroxy-3-oxo-3-pyrrolidin-1-ylpropyl)amide

HRID 751714Notes

Reaction equation

HRID 751714 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:6][C:7]1[CH:8]=[C:9]2[CH:15]=[C:14]([C:16]([NH:18][C@@H:19]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@H:20]([OH:24])[C:21](O)=[O:22])=[O:17])[NH:13][C:10]2=[CH:11][N:12]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C.[Cl-].[Na+].O>[CH2:25]([C@H:19]([NH:18][C:16]([C:14]1[NH:13][C:10]2=[CH:11][N:12]=[C:7]([Cl:6])[CH:8]=[C:9]2[CH:15]=1)=[O:17])[C@H:20]([OH:24])[C:21](=[O:22])[N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 111879523-(S)-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-2-(S)-hydroxy-4-phenylbutyric acid

Product 1

HCID 597536795-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-benzyl-2-(S)-hydroxy-3-oxo-3-pyrrolidin-1-ylpropyl)amide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Pyrrolidine (7 μg, 0.084 mmol) was added to a solution of 3-(S)-[(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-2-(S)-hydroxy-4-phenylbutyric acid (EXAMPLE 124, 30 mg, 0.080 mmol), HOBt (14 mg, 0.091 mmol), DIPEA (31 μL, 0.18 mmol) and EDCI (18 mg, 0.094 mmol) in DMF (3 mL). After stirring for 12 h the mixture was added to diluted brine (100 mL, water/brine: 1/1). Extraction with ethyl acetate (4×25 mL), washing of the combined extracts with brine (50 mL) and drying (MgSO4), gave, after concentration, a residue which was purified by preparative LCMS to give the title compound as a colourless solid. m/z (ES+)=427.31 [M+H]+; RT=3.27 min.

Workup

  1. extractionExtraction with ethyl acetate (4×25 mL)
  2. washwashing of the combined extracts with brine (50 mL)
  3. dry with materialdrying (MgSO4)
  4. customgave
  5. concentrationafter concentration
  6. customa residue which was purified by preparative LCMS

Sources & evidence

ORD record
ord-557e3f9fdaa24955b0893ebb9bd45239
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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