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

HRID 582313ノート

反応式

HRID 582313 の反応式
[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

参加物

6

反応物 4

HCID 8471Triethylamine2 回HCID 62493Pivaloyl chlorideHCID 109595584-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acidHCID 16212813(2S)-2-amino-3-cyclohexylpropan-1-ol hydrochloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
20 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-f7822f3d360143459fdfac427544b875
出典データセット
uspto-grants-1999_07
特許番号
US05922871

反応ノート

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