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 1908260ノート

反応式

HRID 1908260 の反応式
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

参加物

8

反応物 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、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒2 回HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-404cd48260e145f68a2aceddca494596
出典データセット
uspto-grants-2013_12
特許番号
US08598211B2

反応ノート

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