1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66922870, compound

HRID 1622972Notes

Reaction equation

HRID 1622972 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15](O)=[O:16])=[CH:10][CH:9]=2)[C:6](=[O:18])[CH:5]=[CH:4][C:3]=1[C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[F:27].CCN=C=NCCCN(C)C.[CH3:40][C:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])([CH3:43])[NH2:42]>C(Cl)Cl.CN(C=O)C.CN(C1C=CN=CC=1)C.CCOC(C)=O>[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([NH:42][C:41]([CH3:43])([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH3:40])=[O:16])=[CH:10][CH:9]=2)[C:6](=[O:18])[CH:5]=[CH:4][C:3]=1[C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[F:27]

Participants

7

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 7019940tert-Butyl 2-methylalaninate2×HCID 58139016HCID 58139016, compound2×

Product 1

HCID 66922870HCID 66922870, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of {4-[6-amino-5-(2,4-difluorobenzoyl)-2-oxopyridin-1(2H)-yl]phenyl}acetic acid (Intermediate 5) (0.13 g, 0.34 mmol) in DCM/DMF (1:1, 6 ml) were added EDCI (0.07 g, 0.36 mmol), DMAP (0.004 g, 0.03 mmol) followed by the addition of tert-butyl 2-methylalaninate (Intermediate 8) (0.057 g, 0.36 mmol). The mixture was stirred at RT for overnight. The reaction mixture was diluted with EtOAc (20 ml), washed with water (2×20 ml), brine (20 ml), dried (MgSO4), filtered and concentrated under reduced pressure to leave a yellow oil. Purification by column chromatography (100% EtOAc) afforded the title compound as an off-white solid (78 mg, 44% yield).

Workup

  1. washwashed with water (2×20 ml), brine (20 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto leave a yellow oil
  6. customPurification by column chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-8234b30a6d4c4b2d9f5644c1234d1c6d
Source dataset
uspto-grants-2014_07
Patent number
US08778953B2

Reaction notes

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