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Ammonia → N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-1H-benzimidazole-2-carboxamide

HRID 42245
Notes
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Reaction equation

HRID 42245 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([OH:12])=O.[NH:13]1[C:21]2[C:16](=[C:17]([C:22]3[CH:23]=[C:24]([NH2:37])[C:25]4[C:29]([CH:30]=3)=[N:28][N:27](C3CCCCO3)[CH:26]=4)[CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1.CCN(C(C)C)C(C)C.N>CN(C=O)C.CO>[NH:13]1[C:21]2[C:16](=[C:17]([C:22]3[CH:30]=[C:29]4[C:25]([CH:26]=[N:27][NH:28]4)=[C:24]([NH:37][C:10]([C:2]4[NH:1][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[N:3]=4)=[O:12])[CH:23]=3)[CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 2332402-Benzimidazolecarboxylic acidHCID 582679956-(1H-Indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine

Product 1

HCID 44540221N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-1H-benzimidazole-2-carboxamide

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 6228DimethylformamideSolvent

Procedure

1H-Benzimidazole-2-carboxylic acid (available from Apollo Scientific, 25 mg, 0.151 mmol), O-(7-Azabenzatriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (63 mg, 0.17 mmol) and 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (50 mg, 0.15 mmol) were dissolved in anhydrous DMF (3 ml) and then treated with DIPEA (0.05 ml, 0.30 mmol). The reactions were then stirred at room temperature for 15 hours. The mixture was treated with methanol (3 ml) and then Macroporous-Tosic Acid (170 mg, 0.75 mmol) then stirred for 15 hours. The mixture was then treated with 0.88 ammonia solution (0.60 ml), stirred for 10 minutes, then filtered and solvent blown off under a stream of nitrogen. The crude residue was purified by Mass Directed Automated Preparative HPLC (Method B) to give after evaporation of solvents the title compound as a yellow solid (27 mg). LCMS (Method B) m/z 393 [MH+], Rt=1.04 min.

Workup

  1. stirringstirred for 10 minutes
  2. filtrationfiltered
  3. customThe crude residue was purified by Mass Directed Automated Preparative HPLC (Method B)
  4. customto give
  5. customafter evaporation of solvents the title compound as a yellow solid (27 mg)

Sources & evidence

ORD record
ord-faf48123d94743ae808c61a29cfd745c
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536169B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes