4-Methylmorpholine → HCID 86603054、化合物

HRID 855350

反応式

HRID 855350 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=O)[CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH2:14]([O:21][C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][NH:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:34][CH:33]=2)[CH:25]=[CH:26][CH:27]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.O>[CH2:14]([O:21][C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][N:30]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:34][CH:33]=2)[C:11]([C:9]2[CH:10]=[C:2]([Cl:1])[CH:3]=[C:4]3[C:8]=2[NH:7][CH:6]=[CH:5]3)=[O:13])[CH:25]=[CH:26][CH:27]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 668685635-chloro-1H-indole-7-carboxylic acidHCID 68562248[2-(3-Benzyloxy-phenyl)-ethyl]-(4-tert-butyl-benzyl)-amine

生成物 1

HCID 86603054HCID 86603054、化合物収率 90%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 951 mg (4.86 mmol) of 5-chloro-1H-indole-7-carboxylic acid and 1.997 g (5.35 mmol) [2-(3-benzyloxy-phenyl)-ethyl]-(4-tert-butyl-benzyl)-amine in 50 ml DMF, were added 1.6 ml (14.58 mmol) N-methylmorpholine and 2.77 g TBTU (7.29 mmol) at rt. After stirring for 16 h at rt, the reaction mixture was diluted with 300 ml water and extracted with EtOAc (2×). The combined organic phases were washed with twice 200 ml water and 100 ml brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (90 g silica gel; heptane/EtOAc 9:1 then 4:1) to give 2.41 g of 5-chloro-1H-indole-7-carboxylic acid [2-(3-benzyloxy-phenyl)-ethyl]-(4-tert-butyl-benzyl)-amide as a light yellow solid (88%). MS (ISP) 551.3 (M+H)+.

後処理

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic phases were washed with twice 200 ml water and 100 ml brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (90 g silica gel

出典と根拠

ORDレコード
ord-0b2cc513c2e645a197ad1325132743f1
出典データセット
uspto-grants-2007_08
特許番号
US07259183B2

関連ノート

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