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

HRID 749306Notes

Reaction equation

HRID 749306 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-b2a4616cb6cc48769db4756ea5140f64
Source dataset
uspto-grants-2008_07
Patent number
US07402604B2

Reaction notes

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