Diisopropylethylamine → Ethyl 2-hydroxy-4-phenyl-3-(2-(2-phenylthiazol-4-yl)nicotinamido)butanoate

HRID 1400231Notes

Reaction equation

HRID 1400231 reaction equation
Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[C:33]1([C:39]2[S:40][CH:41]=[C:42]([C:44]3[N:52]=[CH:51][CH:50]=[CH:49][C:45]=3[C:46]([OH:48])=O)[N:43]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[Cl-].[CH2:54]([O:56][C:57](=[O:69])[CH:58]([OH:68])[CH:59]([NH3+:67])[CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[CH3:55]>ClCCl>[OH:68][CH:58]([CH:59]([NH:67][C:46](=[O:48])[C:45]1[CH:49]=[CH:50][CH:51]=[N:52][C:44]=1[C:42]1[N:43]=[C:39]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[S:40][CH:41]=1)[CH2:60][C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1)[C:57]([O:56][CH2:54][CH3:55])=[O:69]

Participants

7

Reactant 5

HCID 81531Diisopropylethylamine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67540106(2-Phenylthiazol-4-yl)nicotinic acidHCID 86644788HCID 86644788, compound

Product 1

HCID 67540490Ethyl 2-hydroxy-4-phenyl-3-(2-(2-phenylthiazol-4-yl)nicotinamido)butanoateYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC) (700 mg, 3.65 mmol), 1-hydroxybenzotriazole hydrate (550 mg, 3.59 mmol) and N,N-diisopropylethylamine (DIPEA) (1.2 ml, 6.87 mmol) were successively added to a solution of (2-phenylthiazol-4-yl)nicotinic acid (820 mg, 2.90 mmol) and 4-ethoxy-3-hydroxy-4-oxo-1-phenylbutan-2-aminium chloride (800 mg, 3.08 mmol) in dichloromethane (70 ml) at 5° C., and the mixture stirred at 5° C. for about 5 minutes. A pH of 8 was adjusted by adding 0.6 ml of DIPEA, the mixture stirred for 1 hour at 5° C. and then overnight at room temperature. The mixture then was concentrated under reduced pressure, poured into 200 ml of water, the precipitate formed was filtered off with suction and dried in vacuo to give 1.33 g of the title product as white amorphous solid.

Workup

  1. stirringthe mixture stirred for 1 hour at 5° C.
  2. customovernight
  3. customat room temperature
  4. concentrationThe mixture then was concentrated under reduced pressure
  5. additionpoured into 200 ml of water
  6. customthe precipitate formed
  7. filtrationwas filtered off with suction
  8. customdried in vacuo

Sources & evidence

ORD record
ord-8804e32a46d445349b926fe02932887b
Source dataset
uspto-grants-2014_12
Patent number
US08906941B2

Reaction notes

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