8-Quinolinecarboxylic acid → 1-tert-butoxycarbonyl-2(S)-(2-hydroxyethyl)-4-(8-quinolinylcarbonyl)piperazine

HRID 1598462노트

반응식

HRID 1598462 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([OH:13])=O)[CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[C:36]([O:40][C:41]([N:43]1[CH2:48][CH2:47][NH:46][CH2:45][C@@H:44]1[CH2:49][CH2:50][OH:51])=[O:42])([CH3:39])([CH3:38])[CH3:37]>CN(C=O)C.C(N(CC)CC)C>[C:36]([O:40][C:41]([N:43]1[CH2:48][CH2:47][N:46]([C:11]([C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[N:1]=[CH:2][CH:3]=[CH:4]3)=[O:13])[CH2:45][C@@H:44]1[CH2:49][CH2:50][OH:51])=[O:42])([CH3:39])([CH3:38])[CH3:37]

참가 물질

7

반응물 4

HCID 665828-Quinolinecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12046236(S)-tert-butyl 2-(2-hydroxyethyl)piperazine-1-carboxylate

생성물 1

HCID 228841311-tert-butoxycarbonyl-2(S)-(2-hydroxyethyl)-4-(8-quinolinylcarbonyl)piperazine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

8-Quinoline carboxylic acid (1.00 g, 5.78 mmol), EDC.HCl (1.22 g, 6.38 mmol), HOBT (1.77 g, 13.1 mmol) in DMF at pH 7 (adjusted with triethylamine) was stirred at 20° C. for 15 min. 1-tert-Butoxycarbonyl-2(S)-(2-hydroxyethyl)piperazine (1.33 g, 6.71 mmol) was added and the reaction stirred overnight. DMF was removed in vacuo, and the residue taken up in 1:1:1 THF, methanol, and 5% aqueous sodium hydroxide. This was stirred at 20° C. for 72 h. The volatiles were removed in vacuo, and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was washed with saturated sodium chloride solution, then dried over magnesium sulfate. The title compound was obtained as a foam (1.2 g).

후처리

  1. customDMF was removed in vacuo
  2. stirringThis was stirred at 20° C. for 72 h
  3. customThe volatiles were removed in vacuo
  4. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
  5. washThe organic phase was washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate

출처 및 근거

ORD 기록
ord-2b58dd87d65349509c6a2f376bbbd2e7
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05736539

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