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

HRID 2272575노트

반응식

HRID 2272575 반응식
[CH2:1]([N:4]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[C:8]([NH2:17])[CH:9]=2)[CH2:2][CH3:3].[C:18]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:35])[CH2:28][CH:29]([CH3:34])[CH2:30][C:31](O)=[O:32])=[CH:22][CH:21]=1)#[N:19].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:18]([C:20]1[CH:21]=[CH:22][C:23]([NH:26][C:27](=[O:35])[CH2:28][CH:29]([CH3:34])[CH2:30][C:31]([NH:17][C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[N:4]([CH2:1][CH2:2][CH3:3])[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]3=2)=[O:32])=[CH:24][CH:25]=1)#[N:19]

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 867297339-propyl-2,3,4,9-tetrahydro-1H-carbazol-6-amine

생성물 1

HCID 86729734N-(4-cyanophenyl)-3-methyl-N'-(9-propyl-2,3,4,9-tetrahydro-1H-carbazol-6-yl)pentanediamide수율 33.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of the compound obtained in Step 2 (229 mg, 1.00 mmol), 5-(4-cyanophenylamino)-3-methyl-5-oxopentanoic acid (247 mg, 1.00 mmol) and DIEA (0.525 mL, 3.01 mmol) in DMF (6 mL) was added HATU (572 mg, 1.50 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 (151 mg, 0.332 mmol, 33.1%) 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-88db441f9c7c4cc795422f9a25625605
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120776B2

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