Triethylamine → Ethyl (+/-)-3-phenyl-4-[4-[[[3-(pyridin-2-yl)amino-1-propyl]amino]carbonyl]-1,3-oxazol-2-yl]butanoate

HRID 989902Notes

Reaction equation

HRID 989902 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([CH2:9][CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:7][CH:8]=1)([OH:3])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.CCN(CC)CC.Cl.Cl.[NH2:44][CH2:45][CH2:46][CH2:47][NH:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][N:50]=1>C(Cl)Cl>[C:17]1([CH:10]([CH2:9][C:6]2[O:7][CH:8]=[C:4]([C:1]([NH:44][CH2:45][CH2:46][CH2:47][NH:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][N:50]=3)=[O:3])[N:5]=2)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 11220404HCID 11220404, compoundHCID 6973543799768-43-1

Product 1

HCID 11189784Ethyl (+/-)-3-phenyl-4-[4-[[[3-(pyridin-2-yl)amino-1-propyl]amino]carbonyl]-1,3-oxazol-2-yl]butanoateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl (±)-4-(4-carboxy-1,3-oxazol-2-yl)-3-phenylbutanoate (100 mg, 0.33 mmole) in CH2Cl2 (2 mL) was added 1,1′-carbonyldiimidazole (80 mg, 0.49 mmole). After 2 hr, Et3N (0.14 mL, 0.98 mmole) and 2-[(3-amino-1-propyl)amino]pyridine dihydrochloride (110 mg, 0.49 mmole) were added. After 4 h, the mixture was concentrated under reduced pressure. The residue was chromatographed on silica gel (75% EtOAc/hexanes) to give the title compound (131 mg, 91%) as a yellow oil: MS (ES) m/e 437 (M+H)+.

Workup

  1. waitAfter 4 h
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was chromatographed on silica gel (75% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cedf7ae2cd0a4774bf932733d733c826
Source dataset
uspto-grants-2002_10
Patent number
US06458814B1

Reaction notes

Loading…