Trifluoroacetic acid → HCID 178512588, compound

HRID 2389563Notes

Reaction equation

HRID 2389563 reaction equation
C(OC(=O)[NH:7]/[C:8](/[NH:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([Cl:24])[CH:19]=1)=[N:9]\C(=O)OC(C)(C)C)(C)(C)C.[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29]>ClCCl>[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].[Cl:24][C:20]1[CH:19]=[C:18]([NH:17][C:8]([NH2:9])=[NH:7])[CH:23]=[CH:22][N:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454301tert-butyl N-[[(2-chloro-4-pyridinyl)amino]-[(2-methylpropan-2-yl)oxycarbonylamino]methylidene]carbamate

Product 1

HCID 178512588HCID 178512588, compoundYield 110.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 43.67 g (0.117 mol) of di-tert-butyl{(Z)-[(2-chloropyridin-4-yl)amino]methylylidene}biscarbamate in dichloromethane (800 ml) at room temperature were added 81.64 ml of trifluoroacetic acid (1.06 mol). The reaction mixture was stirred at room temperature for 2 days, concentrated in vacuo, triturated with 100 ml of pentane, and upon standing crystallized to yield 51.68 g of 1-(2-chloropyridin-4-yl)guanidine bis(trifluoroacetate) (yield=99%).

Workup

  1. concentrationconcentrated in vacuo
  2. customtriturated with 100 ml of pentane
  3. customupon standing crystallized

Sources & evidence

ORD record
ord-b8beae96f0734e4e80f91198dfc57f8d
Source dataset
uspto-grants-2012_09
Patent number
US08273759B2

Reaction notes

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