Triethylamine → HCID 66922753, compound

HRID 1622968Notes

Reaction equation

HRID 1622968 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.C(N(CC)CC)C.Cl.[CH3:48][C:49]([C:52]([O:54][CH:55]1[CH2:59][CH2:58][CH2:57][CH2:56]1)=[O:53])([CH3:51])[NH2:50]>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:50][C:49]([CH3:48])([C:52]([O:54][CH:55]3[CH2:56][CH2:57][CH2:58][CH2:59]3)=[O:53])[CH3:51])=[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

8

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 58139016HCID 58139016, compound2×HCID 66616818HCID 66616818, compound2×

Product 1

HCID 66922753HCID 66922753, compoundYield 48.7%

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) (0.1 g, 0.26 mmol) in DCM/DMF (1:1, 6 ml) were added EDCI (0.055 g, 0.29 mmol), DMAP (0.003 g, 0.03 mmol) and triethylamine (40 μl, 0.29 mmol) followed by the addition of cyclopentyl 2-methylalaninate hydrochloride (Intermediate 7) (0.059 g, 0.29 mmol). The mixture was stirred at RT overnight. The reaction mixture was diluted with EtOAc (20 ml), washed with water (2×20 ml), brine (20 ml) then dried (MgSO4), filtered and concentrated under reduced pressure to leave a yellow oil. Purification by column chromatography (100% EtOAc) afforded the title compound as a pale yellow solid (68 mg, 48%)

Workup

  1. washwashed with water (2×20 ml), brine (20 ml)
  2. dry with materialthen dried (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-c344ba7f6b714b8f945d95f6c144eaaf
Source dataset
uspto-grants-2014_07
Patent number
US08778953B2

Reaction notes

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