Diisopropylethylamine → HCID 86590128, compound

HRID 1840514Notes

Reaction equation

HRID 1840514 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C@H:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:12]([OH:14])=O)=[CH:4][CH:3]=1.Cl.[CH2:24]([CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[CH3:25].C(N(CC)C(C)C)(C)C>ClCCl.CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C@H:11]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:12]([CH:27]2[CH:26]([CH2:24][CH3:25])[CH2:31][CH2:30][NH:29][CH2:28]2)=[O:14])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 15521219HCID 15521219, compoundHCID 234481304-Ethylpiperidine--hydrogen chloride (1/1)

Product 1

HCID 86590128HCID 86590128, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.1 g (5.5 mmol) of O-(benzotriazol-1l-yl)-N,N,N′, N′-tetramethyluronium hexafluorophosphate (HBTU) are added portionwise with stirring, at 0° C. under nitrogen, to a mixture of 2.0 g of (S)-6-amino-α-[[(1,1-dimethylethoxy)carbonyl]amino]pyridine-3-pentanoic acid (5.5 mmol), 1.14 g (7.5 mmol) of 4-ethylpiperidine hydrochloride, N,N-diisopropylethylamine (DIEA) (25 ml; 14 mmol) in dichloromethane (30 ml) and 3 ml of anhydrous dimethylformamide (DMF). The mixture is allowed to warm to room temperature and stirring is continued for 18 hours. The reaction mixture is taken up in 250 ml of ethyl acetate and is washed with 50 ml of 0.1 N hydrochloric acid solution and with 50 ml of saturated sodium hydrogen carbonate solution and with 50 ml of saturated sodium chloride solution. The product obtained is then dried over sodium sulphate and then filtered and concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting under pressure with ethyl acetate. 1.48 g of 1,1-dimethylethyl (S)-[4-(6-aminopyrid-3-yl)-1-([4-ethylpiperid-3-yl)carbonyl]butyl]carbamate are obtained in the form of a viscous oil.

Workup

  1. washis washed with 50 ml of 0.1 N hydrochloric acid solution and with 50 ml of saturated sodium hydrogen carbonate solution and with 50 ml of saturated sodium chloride solution
  2. customThe product obtained
  3. dry with materialis then dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica gel
  8. washeluting under pressure with ethyl acetate

Sources & evidence

ORD record
ord-6ac29599a062460e866f808389068838
Source dataset
uspto-grants-2004_01
Patent number
US06680329B2

Reaction notes

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