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 883576노트

반응식

HRID 883576 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 1140Toluene용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-8b5f1db41e784fa4804b6a06661a95ed
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236954B2

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