Dimethylamine, hydrochloride → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-benzyl-2-dimethylcarbamoyl-2-(S)-hydroxyethyl)amide

HRID 751713Notes

Reaction equation

HRID 751713 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[Cl:5][C:6]1[CH:7]=[C:8]2[CH:14]=[C:13]([C:15]([NH:17][C@@H:18]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:19]([OH:23])[C:20]([OH:22])=O)=[O:16])[NH:12][C:9]2=[CH:10][N:11]=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>[CH2:24]([C@H:18]([NH:17][C:15]([C:13]1[NH:12][C:9]2=[CH:10][N:11]=[C:6]([Cl:5])[CH:7]=[C:8]2[CH:14]=1)=[O:16])[C@@H:19]([C:20](=[O:22])[N:3]([CH3:4])[CH3:2])[OH:23])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

8

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 111879523-(S)-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-2-(S)-hydroxy-4-phenylbutyric acid

Product 1

HCID 597537455-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-benzyl-2-dimethylcarbamoyl-2-(S)-hydroxyethyl)amide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Dimethylamine hydrochloride (7 mg, 0.085 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 the addition of DIPEA (14 ml, 0.080 mmol) the mixture was stirred for 12 h before adding 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+)=401.28 [M+H]+; RT=3.06 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-f7d000fea0b6498ba8d8c351683b31cc
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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