Diisopropylethylamine → N-(4-cyanophenyl)-N'-(1-ethyl-2,3-dimethyl-1H-indol-5-yl)-3-methylpentanediamide

HRID 2272557ノート

反応式

HRID 2272557 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:18])[CH2:11][CH:12]([CH3:17])[CH2:13][C:14]([OH:16])=O)=[CH:5][CH:4]=1)#[N:2].[CH2:19]([N:21]1[C:29]2[C:24](=[CH:25][C:26]([NH2:30])=[CH:27][CH:28]=2)[C:23]([CH3:31])=[C:22]1[CH3:32])[CH3:20].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:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:18])[CH2:11][CH:12]([CH3:17])[CH2:13][C:14]([NH:30][C:26]2[CH:25]=[C:24]3[C:29](=[CH:28][CH:27]=2)[N:21]([CH2:19][CH3:20])[C:22]([CH3:32])=[C:23]3[CH3:31])=[O:16])=[CH:7][CH:8]=1)#[N:2]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 3981627HCID 3981627、化合物HCID 64853091-ethyl-2,3-dimethyl-1H-indol-5-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 86729720N-(4-cyanophenyl)-N'-(1-ethyl-2,3-dimethyl-1H-indol-5-yl)-3-methylpentanediamide収率 61.8%

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 1 (510 mg, 2.07 mmol), 1-ethyl-2,3-dimethyl-1H-indol-5-amine (390 mg, 2.07 mmol) and DIEA (1.085 mL, 6.21 mmol) in DMF (8 mL) was added HATU (1181 mg, 3.11 mmol), and the mixture was stirred at room temperature for 14 hr. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was separated, 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; 10 to 100% ethyl acetate/hexane) to give the title compound (533 mg, 1.280 mmol, 61.8%) as a white powder.

後処理

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water and saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-3a4554a564bb447f845a6cfd4cc232be
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…