1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86603723, compound

HRID 2376106Notes

Reaction equation

HRID 2376106 reaction equation
Cl.Cl.[C:3]([O:7][C:8]([N:10]([C@@H:22]1[CH2:26][CH2:25][N:24]([CH2:27][CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH2:23]1)C1N=CC(/C=C/C(O)=O)=CC=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[O:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]1[O:39][NH2:40].O[N:42]1[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=2N=N1.CN(C)CCCN=C=N[CH2:59][CH3:60].C([O-])(O)=[O:63].[Na+]>CN(C)C=O.O>[C:3]([O:7][C:8]([N:10]([C@@H:22]1[CH2:26][CH2:25][N:24]([CH2:27][CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH2:23]1)[C:47]1[CH:48]=[CH:49][C:50](/[CH:45]=[CH:60]/[C:59]([NH:40][O:39][CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38][O:33]2)=[O:63])=[N:42][CH:46]=1)=[O:9])([CH3:4])([CH3:6])[CH3:5]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 68967731HCID 68967731, compound

Product 1

HCID 86603723HCID 86603723, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-1-(2-ethylbutyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylic acid dihydrochloride (303 mg), O-tetrahydro-2H-pyran-2-ylhydroxylamine (109 mg.), and 1-hydroxybenzotriazole (125 mg) in N,N-dimethylformamide (3.1 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (144 mg) at 4° C. The mixture was warmed to ambient temperature and stirred for 8 hours. The reaction mixture was added saturated NaHCO3 (3 mL) and water (12 mL), and extracted with ethyl acetate. The organic layer was washed with H2O and brine, dried over MgSO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give (2E)-3-(5-{(tert-butoxycarbonyl){(3R)-1-(2-ethylbutyl)-3-pyrrolidinyl}amino}-2-pyridinyl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide (135 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-258e04d60d6b4e43b5badc73bb1dfc98
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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