1-Hydroxybenzotriazole → HCID 178423667, 화합물

HRID 1169417노트

반응식

HRID 1169417 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:16][CH2:15][C:14]([C:17](O)=[O:18])=[CH:13][C:12]=3[CH:20]=2)=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.Cl.[CH3:33][N:34]([CH2:41][C@H:42]1[CH2:47][CH2:46][C@H:45]([NH2:48])[CH2:44][CH2:43]1)[CH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.C1CCN2C(=NCCC2)CC1>C(#N)C.C(N(CC)CC)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:16][CH2:15][C:14]([C:17]([NH:48][C@H:45]4[CH2:44][CH2:43][C@H:42]([CH2:41][N:34]([CH3:33])[CH:35]5[CH2:40][CH2:39][O:38][CH2:37][CH2:36]5)[CH2:47][CH2:46]4)=[O:18])=[CH:13][C:12]=3[CH:20]=2)=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 105396746-(4-methylphenyl)-2H-1-benzopyran-3-carboxylic acidHCID 178484107HCID 178484107, 화합물

생성물 1

HCID 178423667HCID 178423667, 화합물수율 53.9%

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 8471Triethylamine용매

실험 절차

Into a suspension of 6-(4-methylphenyl)-2H-1-benzopyran-3-carboxylic acid (150 mg) and 1-hydroxybenzotriazole (114 mg) in acetonitrile (15 ml) was added at room temperature 1-ethyl-3-(340 -dimethylaminopropyl)carbodiimide hydrochloride (162 mg), and the resulting mixture was stirred for 2 hours. Into the reaction mixture was added a solution of trans-4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]cyclohexylamine dihydrochloride (253 mg), 1,8-diazabicyclo[5,4,0]-7-undecene (257 mg) and triethylamine (0.16 ml) in acetonitrile (20 ml), and the resulting mixture was stirred for 5 hours. After the reaction mixture was concentrated under reduced pressure, water was added to the residue, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After the resulting organic layer was concentrated under reduced pressure to remove the solvent, the residue was subjected to purification using column chromatography (ethanol/ethyl acetate 1:1) and to recrystallization (ethyl acetate/hexane) to obtain trans-6-(4-methylphenyl)-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]cyclohexyl]-2H-1-benzopyran-3-carboxamide (compound 67) (144 mg) as colorless crystals.

후처리

  1. stirringthe resulting mixture was stirred for 5 hours
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  6. dry with materialwas dried with magnesium sulfate
  7. concentrationAfter the resulting organic layer was concentrated under reduced pressure
  8. customto remove the solvent
  9. customthe residue was subjected to purification
  10. customto recrystallization (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-4d36ae35ef7741e6b5c16a5aea0d7b2b
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06627651B1

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