1-Hydroxybenzotriazole → 4'-Bromo-2'-[(5-chloro-2-pyridyl)carbamoyl]-6'-hydroxy-1-isopropylpiperidine-4-carboxanilide

HRID 506539노트

반응식

HRID 506539 반응식
[NH2:1][C:2]1[C:17]([OH:18])=[CH:16][C:15]([Br:19])=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1)=[O:5].[CH:20]([N:23]1[CH2:28][CH2:27][CH:26]([C:29](O)=[O:30])[CH2:25][CH2:24]1)([CH3:22])[CH3:21].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[Br:19][C:15]1[CH:16]=[C:17]([OH:18])[C:2]([NH:1][C:29]([CH:26]2[CH2:27][CH2:28][N:23]([CH:20]([CH3:22])[CH3:21])[CH2:24][CH2:25]2)=[O:30])=[C:3]([C:4](=[O:5])[NH:6][C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=2)[CH:14]=1

참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 64841871-Isopropylpiperidine-4-Carboxylic AcidHCID 17856976HCID 17856976, 화합물

생성물 1

HCID 101175564'-Bromo-2'-[(5-chloro-2-pyridyl)carbamoyl]-6'-hydroxy-1-isopropylpiperidine-4-carboxanilide수율 59.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

2-Amino-5-bromo-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide (5.14 g) and 2.83 g of 1-isopropylpiperidine-4-carboxylic acid were dissolved in 75 ml of N,N-dimethylformamide, then 4.33 g of 1-ethyl-3-dimethylaminopropylcarbodiimide hydrochloride and 3.04 g of 1-hydroxybenzotriazole were added thereto and the mixture was stirred at room temperature for 46 hours. The reaction solution was added to 750 ml of 1% aqueous solution of sodium bicarbonate and 200 ml of ethyl acetate were added thereto. Ethyl acetate was evaporated therefrom in vacuo and the resulting solid was collected by filtration and washed with water. The resulting solid was suspended in 100 ml of methanol and 10 ml of water and the suspension was stirred for one night. The resulting precipitate was collected by filtration and dried in vacuo to give 4.41 g of 4′-bromo-2′-[(5-chloro-2-pyridyl)carbamoyl]-6′-hydroxy-1-isopropylpiperidine-4-carboxanilide.

후처리

  1. additionwere added
  2. customEthyl acetate was evaporated
  3. filtrationin vacuo and the resulting solid was collected by filtration
  4. washwashed with water
  5. stirring10 ml of water and the suspension was stirred for one night
  6. filtrationThe resulting precipitate was collected by filtration
  7. customdried in vacuo

출처 및 근거

ORD 기록
ord-2ed13476df4d4fb28f856bf7dbd360f1
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786106B2

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