Acetonitrile → HCID 178523263, compound

HRID 2064627Notes

Reaction equation

HRID 2064627 reaction equation
[C:1]([CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:25]=[CH:24][C:11]2[NH:12][C:13]([C:15]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:17][N:16]=3)=[N:14][C:10]=2[CH:9]=1)=[O:7])#[N:2].[N:26]([Sn](CCCC)(CCCC)CCCC)=[N+:27]=[N-:28].C(#N)C.O1CCCC1>C(O)(=O)C>[N:2]1[NH:26][N:27]=[N:28][C:1]=1[CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:25]=[CH:24][C:11]2[NH:12][C:13]([C:15]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:17][N:16]=3)=[N:14][C:10]=2[CH:9]=1)=[O:7]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 4984872Tributyltin azideHCID 178511132HCID 178511132, compound

Product 1

HCID 178523263HCID 178523263, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 2-(1H-indazol-3-yl)-1H-benzoimidazole-5-carboxylic acid (2-cyano-ethyl)-amide [150 mg, Example 246(s)] and azidotributyltin (2 ml) was heated at 95° C. for 24 hours. The reaction was cooled to ambient temperature and stirred for 2 hours with acetonitrile (20 ml), tetrahydrofuran (10 ml) and acetic acid (20 ml). The reaction mixture was washed with iso-hexane (6×80 ml) and concentrated in vacuo. The residue was subjected to preparative HPLC to give 2-(1H-indazol-3-yl)-1H-benzoimidazole-5-carboxylic acid [2-(2H-tetrazol-5-yl)-ethyl]-amide (35.9 mg) as a brown solid.

Workup

  1. washThe reaction mixture was washed with iso-hexane (6×80 ml)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3aa2cf098b644aba940d6c334c387c6f
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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