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 349199Notes

Reaction equation

HRID 349199 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](NC)[C:40]2[C:45]([CH:46]=1)=[CH:44][CH:43]=[CH:42][CH:41]=2.O.[CH2:50]([N:52](CC)CC)C>CN(C)C=O>[CH3:36][C:37]1[N:38]=[C:39]([CH2:50][NH:52][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 5

HCID 962WaterHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 668062433-Methyl-isoquinolin-1-yl-methylamineHCID 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 1

HCID 6228DimethylformamideSolvent

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-yl-methylamine 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-c3e4892db9234b5b8b0dd242c40c9f0a
Source dataset
uspto-grants-2007_02
Patent number
US07179809B2

Reaction notes

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