Hydrochloric Acid → Methyl 5-({2-amino-5-[(4-methyl-1-piperazinyl)methyl]phenyl}amino)-3-({(1R)-1-[2-(trifluoromethyl)phenyl]ethyl}oxy)-2-thiophenecarboxylate

HRID 883576Notes

Reaction equation

HRID 883576 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([N+:38]([O-])=O)=[C:13]([NH:15][C:16]3[S:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[C:18]([O:25][C@@H:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]([F:37])([F:36])[F:35])[CH3:27])[CH:17]=3)[CH:14]=2)[CH2:4][CH2:3]1.Cl.COC(OC)OC>C1(C)C=CC=CC=1.[Pd]>[NH2:38][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:14][C:13]=1[NH:15][C:16]1[S:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[C:18]([O:25][C@@H:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([F:35])([F:37])[F:36])[CH3:27])[CH:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 9005Trimethyl orthoformateHCID 44185548(R)-Methyl 5-((5-((4-methylpiperazin-1-yl)methyl)-2-nitrophenyl)amino)-3-(1-(2-(trifluoromethyl)phenyl)ethoxy)thiophene-2-carboxylate

Product 1

HCID 57538942Methyl 5-({2-amino-5-[(4-methyl-1-piperazinyl)methyl]phenyl}amino)-3-({(1R)-1-[2-(trifluoromethyl)phenyl]ethyl}oxy)-2-thiophenecarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of methyl 5-({5-[(4-methyl-1-piperazinyl)methyl]-2-nitrophenyl}amino)-3-({(1R)-1-[2-(trifluoromethyl)phenyl]ethyl}oxy)-2-thiophenecarboxylate (0.24 g, 0.415 mmol), 5% Pd/C (0.144 g), HCl (1.25 M in MeOH, 0.034 mL, 0.043 mmol), trimethylorthoformate (1.66 mL, 15.2 mmol) in toluene (0.58 mL) was hydrogenated under a H2 atmosphere at 1.1 bar pressure overnight. The vessel was purged with N2 and the reaction mixture was analysed by HPLC to confirm presence of the title compound which was not purified, but used crude in the next step. LRMS found m/z [ES+] 549.

Workup

  1. customwas hydrogenated under a H2 atmosphere at 1.1 bar pressure overnight
  2. customThe vessel was purged with N2
  3. customwas not purified

Sources & evidence

ORD record
ord-8b5f1db41e784fa4804b6a06661a95ed
Source dataset
uspto-grants-2012_08
Patent number
US08236954B2

Reaction notes

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