Water → 2-Methylpentane

HRID 1693455Notes

Reaction equation

HRID 1693455 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].CC[N:18]([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20].C1C=C[C:28]2[N:33](O)N=[N:31][C:29]=2[CH:30]=1.[OH2:35].CCN=C=NCCCN(C)C>CN(C=O)C>[CH3:4][CH2:3][CH2:9][CH:10]([CH3:15])[CH3:11].[CH3:7][N:6]([CH3:8])[C:4]([C@@H:3]([NH:2][C:21]([C:19]1[NH:18][C:22]2=[CH:23][N:31]=[C:29]([C:28]#[N:33])[CH:30]=[C:24]2[CH:20]=1)=[O:35])[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:5]

Participants

8

Reactant 5

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 12653778(2S)-2-Amino-N,N-dimethyl-3-phenylpropanamide hydrochloride

Product 2

HCID 78922-MethylpentaneHCID 112106335-Cyano-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-dimethylcarbamoyl-2-phenylethyl)amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(S)-amino-N,N-dimethyl-3-phenylpropionamide hydrochloride (Preparation 8, 0.023 g, 0.100 mmol) in DMF (anhydrous, 4 mL) was added DIPEA (0.052 mL, 0.300 mmol) then carboxylic acid (Preparation 62, 0.017 g, 0.091 mmol). To the stirred solution was added HOBt.H2O (0.0135 g, 0.100 mmol) then, after 10 min, EDCI (0.021 g, 0.109 mmol). The reaction mixture was stirred for 18 h then all volatiles were removed in vacuo. The residue was partitioned between ethyl acetate (30 mL) and water (20 mL). The layers were separated and the aqueous layer extracted with ethyl acetate (3×20 mL). The combined organics were washed with brine (30 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in ethyl acetate then adsorbed onto silica gel. Purification via flash column chromatography (SiO2, ethyl acetate:isohexane, 1:1, v/v) gave the title compound as a pale brown solid. δH (CDCl3): 2.77 (3H, s), 2.96 (3H, s), 3.08-8.20 (2H, m), 5.23-5.41 (1H, m), 6.99 (1H, s), 7.14-7.36 (5H, m), 7.65 (1H, d), 8.01 (1H, s), 8.87 (1H, s), 10.01 (1H, s); m/z (ES+)=362 [M+H]+; RT=3.11 min.

Workup

  1. customall volatiles were removed in vacuo
  2. customThe residue was partitioned between ethyl acetate (30 mL) and water (20 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with ethyl acetate (3×20 mL)
  5. washThe combined organics were washed with brine (30 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue was dissolved in ethyl acetate
  10. customPurification via flash column chromatography (SiO2, ethyl acetate

Sources & evidence

ORD record
ord-12266700926d4b1681fa8942a2525f2a
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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