Triethylamine → 1-[N-[(1S)-1-(Cyclohexylmethyl)-2-hydroxyethyl]carbamoyl]-4-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzene

HRID 582313노트

반응식

HRID 582313 반응식
[CH:1]([NH:4][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][CH:20]=3)=[O:18])[CH2:13][CH2:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.Cl.[NH2:43][C@@H:44]([CH2:47][CH:48]1[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1)[CH2:45][OH:46]>C(Cl)Cl>[CH:48]1([CH2:47][C@H:44]([NH:43][C:23]([C:22]2[CH:26]=[CH:27][C:19]([C:17]([N:14]3[CH2:15][CH2:16][N:11]([C:6]4[C:5]([NH:4][CH:1]([CH3:2])[CH3:3])=[CH:10][CH:9]=[CH:8][N:7]=4)[CH2:12][CH2:13]3)=[O:18])=[CH:20][CH:21]=2)=[O:25])[CH2:45][OH:46])[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1

참가 물질

6

반응물 4

HCID 8471Triethylamine2회HCID 62493Pivaloyl chlorideHCID 109595584-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acidHCID 16212813(2S)-2-amino-3-cyclohexylpropan-1-ol hydrochloride

생성물 1

HCID 573068291-[N-[(1S)-1-(Cyclohexylmethyl)-2-hydroxyethyl]carbamoyl]-4-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzene수율 100.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
20 °C

실험 절차

4-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acid (1.5 g) was dissolved in methylene chloride (60 ml) and then, triethylamine (0.7 ml) was added and cooled. Pivaloyl chloride (0.58 ml) was added slowly to the solution at 0~5° C. and the mixture was stirred at SoC for 2 hours. And then triethylamine (1.7 ml) and (S)-(+)-2-amino-3-cyclohexyl-1-propanol hydrochloride (0.87 g) were added in order, the solution was stirred at 0° C. for 3 hours and heated slowly to 20° C. and stirred for 1 hour. The reaction mixture was washed with water twice and the solvent was concentrated under reduced pressure. The concentrated residue was recrystallized using isopropanol and ether. The recrystallized product was filtered and dried to give 2.07 g (yield: 80%) of the desired compound. m.p.: 139~140° C.; 1H-NMR(CDCl3), ppm: δ 0.89~1.01(m, 2H), 1.22(m, 9H), 1.34(m, 1H), 1.45(m, 2H), 1.71(m, 4H), 1.81(m, 1H), 3.10(m, 4H), 3.51(m, 3H), 3.61(m, 1H), 3.76(m, 1H), 3.89(m, 2H), 4.13(m, 1H), 4.26(m, 1H), 6.59(m, 1H), 6.83(m, 1H), 6.95(m, 1H), 7.40(m, 2H), 7.67(m, 1H), 7.77(m, 2H)

후처리

  1. temperaturecooled
  2. stirringthe solution was stirred at 0° C. for 3 hours
  3. stirringstirred for 1 hour
  4. washThe reaction mixture was washed with water twice
  5. concentrationthe solvent was concentrated under reduced pressure
  6. customThe concentrated residue was recrystallized
  7. filtrationThe recrystallized product was filtered
  8. customdried

출처 및 근거

ORD 기록
ord-f7822f3d360143459fdfac427544b875
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05922871

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