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

HRID 1829789
Notes
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Reaction equation

HRID 1829789 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 9949122
N-(4-Dimethylaminobenzyl) 4-hydroxy-1-methyl-1H-indole-2-carboxamide
Yield 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-948d5e8d7ae449a797f928009af57089
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07064143B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes