Water → 2-bromo-3-(2-butyn-1-yl)-5-(trans-2-methoxy-vinyl)-3H-imidazole-4-carboxylic acid-(3-methyl-isoquinolin-1-ylmethyl)-amide

HRID 1453546Notes

Reaction equation

HRID 1453546 reaction equation
[Br:1][C:2]1[NH:6][C:5]([C:7]([OH:9])=O)=[C:4](/[CH:10]=[CH:11]/[O:12][CH3:13])[N:3]=1.CN(C(ON1N=N[C:24]2[CH:25]=CC=[CH:28][C:23]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:36][C:37]1[N:38]=[C:39]([CH2:47][NH2:48])[C:40]2[C:45]([CH:46]=1)=[CH:44][CH:43]=[CH:42][CH:41]=2.O>C(N(CC)CC)C.CN(C)C=O>[CH3:36][C:37]1[N:38]=[C:39]([CH2:47][NH:48][C:7]([C:5]2[N:6]([CH2:28][C:23]#[C:24][CH3:25])[C:2]([Br:1])=[N:3][C:4]=2/[CH:10]=[CH:11]/[O:12][CH3:13])=[O:9])[C:40]2[C:45]([CH:46]=1)=[CH:44][CH:43]=[CH:42][CH:41]=2

Participants

7

Reactant 4

HCID 962WaterHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 215066303-Methyl-isoquinolin-1-ylmethylamineHCID 178494817HCID 178494817, compound

Product 1

HCID 689749602-bromo-3-(2-butyn-1-yl)-5-(trans-2-methoxy-vinyl)-3H-imidazole-4-carboxylic acid-(3-methyl-isoquinolin-1-ylmethyl)-amide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 3.50 g 2-bromo-5-(trans-2-methoxy-vinyl)-3H-imidazole-4-carboxylic acid and 1.30 g TBTU in 1.20 ml triethylamine and 30 ml of dimethylformamide is stirred for 15 min at ambient temperature. Then 1.09 g 3-methyl-isoquinolin-1-ylmethylamine are added, and the resulting suspension is stirred for 4 h at ambient temperature. Then ice-cooled water is added and the precipitate is separated off. The precipitate is dissolved in dichloromethane, the solution is dried over sodium sulphate and the solvent is removed.

Workup

  1. additionis added
  2. customthe precipitate is separated off
  3. dissolutionThe precipitate is dissolved in dichloromethane
  4. dry with materialthe solution is dried over sodium sulphate
  5. customthe solvent is removed

Sources & evidence

ORD record
ord-10f19dfeff4a4566a862f23fdec16645
Source dataset
uspto-grants-2009_01
Patent number
US07476671B2

Reaction notes

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