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1-Hydroxybenzotriazole → N-(4-Dimethylaminobenzyl) 4-hydroxy-1-methyl-1H-indole-2-carboxamide

HRID 1829789
ノート
印刷プレビュー

反応式

HRID 1829789 の反応式
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([OH:14])=O)[N:6]2[CH3:11].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.Cl.[CH3:58][N:59]([CH3:68])[C:60]1[CH:67]=[CH:66][C:63]([CH2:64][NH2:65])=[CH:62][CH:61]=1>CN(C=O)C>[CH3:58][N:59]([CH3:68])[C:60]1[CH:67]=[CH:66][C:63]([CH2:64][NH:65][C:12]([C:5]2[N:6]([CH3:11])[C:7]3[C:3]([CH:4]=2)=[C:2]([OH:1])[CH:10]=[CH:9][CH:8]=3)=[O:14])=[CH:62][CH:61]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27346334-(aminomethyl)-N,N-dimethylaniline dihydrochlorideHCID 102197584-Hydroxy-1-methyl-1H-indole-2-carboxylic acid

生成物 1

HCID 9949122
N-(4-Dimethylaminobenzyl) 4-hydroxy-1-methyl-1H-indole-2-carboxamide
収率 69%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-hydroxy-1-methyl-1H-indole-2-carboxylic acid (Example 10, 0.12 g) in DMF (10 mL) was added TBTU (0.20 g), HOBt (0.10 g) and DIEA (0.35 mL). After 5 min. 4-(dimethylamino)benzylamine dihydrochloride (0.14 g) was added and stirring was continued overnight under nitrogen at room temperature. The residue remaining after DMF evaporation was purified by reversed phased chromatography on C18 silica with a trifluoroacetic acid (0.025%) acidified acetonitrile water gradient to give 0.14 g of the title compound. MS ES (M++H)=324.

後処理

  1. waitwas continued overnight under nitrogen at room temperature
  2. customafter DMF evaporation
  3. customwas purified

出典と根拠

ORDレコード
ord-948d5e8d7ae449a797f928009af57089
出典データセット
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07064143B1

反応ノート

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