Triethylamine → HCID 86707231, compound

HRID 2174670Notes

Reaction equation

HRID 2174670 reaction equation
Cl.CN(C)CCCN=C=NCC.CCN(CC)CC.[N:20]1[N:21]([C:29]2[N:50]=[CH:49][CH:48]=[CH:47][C:30]=2[C:31]([NH:33][CH:34]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:35]([OH:39])[C:36](O)=[O:37])=[O:32])[CH:22]=[C:23]2[C:28]=1[CH:27]=[CH:26][CH:25]=[CH:24]2.Cl.[CH3:52][O:53][NH2:54]>CN(C=O)C>[OH:39][CH:35]([C:36]([NH:54][O:53][CH3:52])=[O:37])[CH:34]([NH:33][C:31](=[O:32])[C:30]1[CH:47]=[CH:48][CH:49]=[N:50][C:29]=1[N:21]1[CH:22]=[C:23]2[C:28]([CH:27]=[CH:26][CH:25]=[CH:24]2)=[N:20]1)[CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 521874O-Methylhydroxylamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67958233HCID 67958233, compound

Product 1

HCID 86707231HCID 86707231, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (663 mg, 3.46 mmol) and Et3N (0.900 ml, 6.46 mmol) were successively added to a solution of 3-[2-(2H-indazol-2-yl)nicotinamido]-2-hydroxy-4-phenylbutanoic acid (1200 mg, 2.88 mmol) and O-methylhydroxylamine hydrochloride (0.350 ml, 4.61 mmol) in DMF (35 ml) at 5° C., and the mixture was stirred for 5 minutes. A pH of 10 was adjusted by adding Et3N (0.643 ml, 4.61 mmol), stirring was continued for 1 hour at 5° C. and then overnight at room temperature. The reaction mixture was then concentrated under reduced pressure. To the obtained residue were added water (150 ml) and a saturated aqueous solution of NaHCO3 (20 ml) with stirring. Following stirring for about 20 minutes the precipitate formed was filtered off with suction and treated with methyl-tert.-butylether (40 ml) to give, after filtration and drying in vacuo, 1.07 g of the title compound as an off-white solid.

Workup

  1. stirringstirring
  2. waitwas continued for 1 hour at 5° C.
  3. customovernight
  4. customat room temperature
  5. concentrationThe reaction mixture was then concentrated under reduced pressure
  6. additionTo the obtained residue were added water (150 ml)
  7. stirringa saturated aqueous solution of NaHCO3 (20 ml) with stirring
  8. stirringFollowing stirring for about 20 minutes the precipitate
  9. customformed
  10. filtrationwas filtered off with suction
  11. additiontreated with methyl-tert.-butylether (40 ml)
  12. customto give
  13. filtrationafter filtration
  14. dry with materialdrying in vacuo, 1.07 g of the title compound as an off-white solid

Sources & evidence

ORD record
ord-d2467fbd95c74c7f8db5b8bb98cda7aa
Source dataset
uspto-grants-2015_06
Patent number
US09062027B2

Reaction notes

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