3-Aminobenzonitrile → HCID 178509851, compound

HRID 1406438Notes

Reaction equation

HRID 1406438 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:14][C:13]2[CH:15]=[CH:16][C:17]([C:19]([OH:21])=O)=[CH:18][C:12]=2[N:11]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:44][C:45]1[CH:46]=[C:47]([CH:50]=[CH:51][CH:52]=1)[C:48]#[N:49]>>[C:48]([C:47]1[CH:46]=[C:45]([NH:44][C:19]([C:17]2[CH:16]=[CH:15][C:13]3[NH:14][C:10]([NH:9][C:3]4[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])=[N:11][C:12]=3[CH:18]=2)=[O:21])[CH:52]=[CH:51][CH:50]=1)#[N:49]

Participants

4

Reactant 3

HCID 167023-AminobenzonitrileHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178524175HCID 178524175, compound

Product 1

HCID 178509851HCID 178509851, compound

Procedure

To 2-(2,6-dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (32 mg, 0.1 mmol) in DMF TEA (50 μL, 0.36 mmol) and TBTU (32.1 mg, 0.1 mmol) were added, followed by 3-amino-benzonitrile (11.8 mg, 0.1 mmol). After shaking overnight at room temperature, the solvent was removed i.vac. and the residue purified by preparative reverse phase chromatography (gradient H2O/AcCN=90:10 to 35:65; both solvents containing 0.1% TFA).

Workup

  1. customthe solvent was removed i.vac
  2. customand the residue purified by preparative reverse phase chromatography (gradient H2O/AcCN=90:10 to 35:65
  3. additionboth solvents containing 0.1% TFA)

Sources & evidence

ORD record
ord-4215914a6da245f388c0f20fee62dda3
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

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