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

HRID 2272575ノート

反応式

HRID 2272575 の反応式
[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]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 3981627HCID 3981627、化合物HCID 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-88db441f9c7c4cc795422f9a25625605
出典データセット
uspto-grants-2015_09
特許番号
US09120776B2

反応ノート

読み込み中…