Diisopropylethylamine → N-(4-cyanophenyl)-3-methyl-N'-[9-(2-methylpropyl)-2,3,4,9-tetrahydro-1H-carbazol-6-yl]pentanediamide

HRID 2272578노트

반응식

HRID 2272578 반응식
[CH2:1]([N:5]1[C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([NH2:18])[CH:10]=2)[CH:2]([CH3:4])[CH3:3].[C:19]([C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:36])[CH2:29][CH:30]([CH3:35])[CH2:31][C:32](O)=[O:33])=[CH:23][CH:22]=1)#[N:20].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[C:19]([C:21]1[CH:22]=[CH:23][C:24]([NH:27][C:28](=[O:36])[CH2:29][CH:30]([CH3:35])[CH2:31][C:32]([NH:18][C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]3=2)=[O:33])=[CH:25][CH:26]=1)#[N:20]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 3981627HCID 3981627, 화합물HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867297369-isobutyl-2,3,4,9-tetrahydro-1H-carbazol-6-amine

생성물 1

HCID 86729737N-(4-cyanophenyl)-3-methyl-N'-[9-(2-methylpropyl)-2,3,4,9-tetrahydro-1H-carbazol-6-yl]pentanediamide수율 53.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of the compound obtained in Step 2 (235 mg, 0.97 mmol), 5-(4-cyanophenylamino)-3-methyl-5-oxopentanoic acid (239 mg, 0.97 mmol) and DIEA (0.508 mL, 2.91 mmol) in DMF (6 mL) was added HATU (553 mg, 1.45 mmol), and the mixture was stirred at room temperature for 14 hr. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5 to 75% ethyl acetate/hexane) to give the title compound (242 mg, 0.515 mmol, 53.1%) as a white powder.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 5 to 75% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-ce24647ba16446d6857f46401542d9c7
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120776B2

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