Benzylamine → HCID 178522795, compound

HRID 2064570Notes

Reaction equation

HRID 2064570 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1C2C(=CC=CC=2)C([C:34]2[NH:38][C:37]3[CH:39]=[CH:40][C:41]([C:43]([OH:45])=O)=[CH:42][C:36]=3[N:35]=2)=N1.[CH2:46]([NH2:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O.CS(C)=O>[CH2:46]([NH:53][C:43]([C:41]1[CH:40]=[CH:39][C:37]2[NH:38][CH:34]=[N:35][C:36]=2[CH:42]=1)=[O:45])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524162HCID 178524162, compound

Product 1

HCID 178522795HCID 178522795, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent3×

Conditions

Temperature
20 °C

Procedure

A solution of 27.3 mg of HBTU in 0.2 ml of dimethylformamide is added, at a temperature in the region of 20° C., to a solution of 20 mg of 2-(1H-indazol-3-yl)-1H-benzimidazole-5-carboxylic acid in 0.42 ml of anhydrous dimethylformamide. After stirring at a temperature in the region of 20° C. for one hour, 15.7 ml of benzylamine are added, followed by addition of 12.4 ml of N,N-diisopropylethylamine dissolved in 0.32 ml of dimethylformamide. After 20 hours, at a temperature in the region of 20° C., the reaction medium is concentrated under reduced pressure, at a temperature in the region of 40° C. The crude residue obtained is dissolved in DMSO and purified by preparative LC-MS. The fractions containing the desired product are combined and concentrated under reduced pressure at a temperature in the region of 40° C. 20 mg of 21H-indazol-3-yl)-1H-benzimidazole-5-carboxylic acid benzylamide are thus obtained in the form of a cream-coloured powder, the characteristics of which are as follows:

Workup

  1. waitAfter 20 hours
  2. concentrationat a temperature in the region of 20° C., the reaction medium is concentrated under reduced pressure, at a temperature in the region of 40° C
  3. customThe crude residue obtained
  4. custompurified by preparative LC-MS
  5. additionThe fractions containing the desired product
  6. concentrationconcentrated under reduced pressure at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-cb58e3c9788f4a8283d88a53c4c8182d
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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