1H-Indole-7-carboxylic acid → 1H-Indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(tetrahydro-thiopyran-4-yl)-ethyl]-amide

HRID 855343

反応式

HRID 855343 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([OH:12])=O)[CH:3]=[CH:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.[C:44]([C:48]1[CH:63]=[CH:62][C:51]([CH2:52][NH:53][CH2:54][CH2:55][CH:56]2[CH2:61][CH2:60][S:59][CH2:58][CH2:57]2)=[CH:50][CH:49]=1)([CH3:47])([CH3:46])[CH3:45]>CN(C=O)C.O>[C:44]([C:48]1[CH:63]=[CH:62][C:51]([CH2:52][N:53]([CH2:54][CH2:55][CH:56]2[CH2:61][CH2:60][S:59][CH2:58][CH2:57]2)[C:10]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]=2[NH:1][CH:2]=[CH:3]3)=[O:12])=[CH:50][CH:49]=1)([CH3:47])([CH3:45])[CH3:46]

参加物

7

反応物 4

HCID 742811H-Indole-7-carboxylic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69342005(4-Tert-butyl-benzyl)-[2-(tetrahydro-thiopyran-4-yl)-ethyl]-amine

生成物 1

HCID 866030481H-Indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(tetrahydro-thiopyran-4-yl)-ethyl]-amide収率 102.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 48 mg (0.3 mmol) of 1H-indole-7-carboxylic acid and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 78 mg (0.3 mmol) of (4-tert-butyl-benzyl)-[2-(tetrahydro-thiopyran-4-yl)-ethyl]-amine in 1 ml DMF were added. After stirring for 24 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo to give 134 mg (99%) of a yellow solid. MS (ISP) 435.5 (M+H)+.

後処理

  1. stirringAfter stirring for 24 h at rt
  2. extractionextracted with 2×50 ml EtOAc
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-94597b69c7764a23a861de87a0601d07
出典データセット
uspto-grants-2007_08
特許番号
US07259183B2

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