Trifluoroacetic acid → Ethyl 6-[2-benzyloxy-5-bromobenzylamino]-3-pyridazinecarboxylate

HRID 1455990Notes

Reaction equation

HRID 1455990 reaction equation
[CH2:1]([O:8][C:9]1[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][C:10]=1[CH2:11][N:12]([C:20]1[N:25]=[N:24][C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:21]=1)C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][C:10]=1[CH2:11][NH:12][C:20]1[N:25]=[N:24][C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:21]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22105523Ethyl 6-[N-(2-benzyloxy-5-bromobenzyl)-N-(tert-butoxycarbonyl)amino]-3-pyridazinecarboxylate

Product 1

HCID 22105509Ethyl 6-[2-benzyloxy-5-bromobenzylamino]-3-pyridazinecarboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 6-[N-(2-benzyloxy-5-bromobenzyl)-N-(tert-butoxycarbonyl)amino]-3-pyridazinecarboxylate (2.0 g) and trifluoroacetic acid (25 ml) in CH2Cl2 (25 ml) was allowed to stand for 18 hours. The solvents were evaporated, the residue dissolved in CH2Cl2 and washed with dilute aqueous Na2CO3 solution, dried (MgSO4) and evaporated to give ethyl 6-[2-benzyloxy-5-bromobenzylamino]-3-pyridazinecarboxylate as a solid (1.5 g).

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue dissolved in CH2Cl2
  3. washwashed with dilute aqueous Na2CO3 solution
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-39b2d114c0544e7c992378c21d71dde2
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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