1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Ethyl 3-(2-(3-(4-fluorophenyl)-1H-pyrazol-1-yl)nicotinamido)-2-hydroxy-4-phenylbutanoate

HRID 1908260노트

반응식

HRID 1908260 반응식
Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[F:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:35]=[CH:34][N:33]([C:36]3[N:44]=[CH:43][CH:42]=[CH:41][C:37]=3[C:38]([OH:40])=O)[N:32]=2)=[CH:27][CH:26]=1.[Cl-].[CH2:46]([O:48][C:49](=[O:61])[CH:50]([OH:60])[CH:51]([NH3+:59])[CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[CH3:47]>ClCCl.COC(C)(C)C.CCN(CC)CC>[F:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]2[CH:35]=[CH:34][N:33]([C:36]3[N:44]=[CH:43][CH:42]=[CH:41][C:37]=3[C:38]([NH:59][CH:51]([CH2:52][C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)[CH:50]([OH:60])[C:49]([O:48][CH2:46][CH3:47])=[O:61])=[O:40])[N:32]=2)=[CH:29][CH:30]=1

참가 물질

8

반응물 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 672388002-(3-(4-fluorophenyl)-1H-pyrazol-1-yl)nicotinic acidHCID 86644788HCID 86644788, 화합물

생성물 1

HCID 67239028Ethyl 3-(2-(3-(4-fluorophenyl)-1H-pyrazol-1-yl)nicotinamido)-2-hydroxy-4-phenylbutanoate수율 69.4%

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매2회HCID 15413tert-Butyl methyl ether용매

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온도
5 °C

실험 절차

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC) (4.47 g, 23.3 mmol), 1-hydroxybenzotriazole hydrate (HOBt) (3.57 g, 23.3 mmol) and triethylamine (Et3N) (4.5 ml, 32.3 mmol) were successively added to a solution of 2-(3-(4-fluorophenyl)-1H-pyrazol-1-yl)nicotinic acid (6.0 g, 21.8 mmol) and 4-ethoxy-3-hydroxy-4-oxo-1-phenylbutan-2-aminium chloride (6.60 g, 25.4 mmol) in dichloromethane (300 ml) at 5° C., and the mixture was stirred at 5° C. for about 5 minutes. A pH of 10 was adjusted by adding 6 ml Et3N, the mixture stirred for 1 h at 5° C. and then overnight at room temperature. The mixture then was concentrated under reduced pressure, poured into 1000 ml of water, the precipitate formed was filtered off with suction and dried in vacuo to give 7.8 g, which were treated 100 ml of methyl-tert.butylether to give 7.39 g of the desired product; ESI-MS [M+H]+: 489.2.

후처리

  1. stirringthe mixture stirred for 1 h at 5° C.
  2. customovernight
  3. customat room temperature
  4. concentrationThe mixture then was concentrated under reduced pressure
  5. additionpoured into 1000 ml of water
  6. customthe precipitate formed
  7. filtrationwas filtered off with suction
  8. customdried in vacuo
  9. customto give 7.8 g, which

출처 및 근거

ORD 기록
ord-404cd48260e145f68a2aceddca494596
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598211B2

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