1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 76852798, compound

HRID 1693404Notes

Reaction equation

HRID 1693404 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([OH:13])=O)[NH:8][C:5]2=[CH:6][N:7]=1.[C:14]1([CH2:20][C@H:21]([NH2:33])[C:22]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:26][CH2:25][CH2:24][O:23]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=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>[C:14]1([CH2:20][C@H:21]([NH:33][C:11]([C:9]2[NH:8][C:5]3=[CH:6][N:7]=[C:2]([Cl:1])[CH:3]=[C:4]3[CH:10]=2)=[O:13])[C:22]2([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[O:26][CH2:25][CH2:24][O:23]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 446307045-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acidHCID 59753663HCID 59753663, compound

Product 1

HCID 76852798HCID 76852798, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 18, 88 mg, 0.403 mmol) and 2-phenyl-1-(S)-(2-phenyl-[1,3]dioxolan-2-yl)ethylamine (Preparation 95, 104 mg, 0.386 mmol) in DMF (5 mL) was added HOBt (65 mg, 0.424 mmol), DIPEA (0.155 mL, 0.890 mmol) and EDCI (90 mg, 0.469 mmol). After stirring at rt 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 diluted hydrochloric acid (1M, 30 ml), diluted aqueous sodium hydroxide solution (1M, 30 ml) and brine (50 mL) followed by drying (MgSO4) gave after concentration a residue which was purified by flash chromatography on silica gel (eluent: hexane/ethyl acetate: 50/50). The title compound was obtained as a colourless oil. δH (CDCl3): 2.73 (1H, dd), 3.10 (1H, dd), 3.84-4.22 (4H, 4m), 5.01 (1H, ddd), 6.37 (1H, d), 6.72 (1H, s), 7.05-7.62 (11H, 3m), 8.64 (1H, s), 10.48 (1H, s); m/z (ES+)=448.24 [M+H]+; RT=3.64 min.

Workup

  1. extractionExtraction with ethyl acetate (4×25 mL)
  2. washwashing of the combined extracts with diluted hydrochloric acid (1M, 30 ml), diluted aqueous sodium hydroxide solution (1M, 30 ml) and brine (50 mL)
  3. dry with materialby drying (MgSO4)
  4. customgave
  5. concentrationafter concentration a residue which
  6. customwas purified by flash chromatography on silica gel (eluent: hexane/ethyl acetate: 50/50)

Sources & evidence

ORD record
ord-020096e1baee42cc8be19249305d4efb
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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