Water → Phenylmethyl4-{1-[2-chloro-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-1-piperazinecarboxylate

HRID 419429노트

반응식

HRID 419429 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1F.C([O-])([O-])=O.[K+].[K+].FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[NH:34]1[CH2:39][CH2:38][CH:37]([N:40]2[CH2:45][CH2:44][N:43]([C:46]([O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[O:47])[CH2:42][CH2:41]2)[CH2:36][CH2:35]1.O>CS(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:34]1[CH2:39][CH2:38][CH:37]([N:40]2[CH2:41][CH2:42][N:43]([C:46]([O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[O:47])[CH2:44][CH2:45]2)[CH2:36][CH2:35]1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 534032891-Chloro-2-fluoro-4-methoxy-5-nitrobenzeneHCID 86625193Phenylmethyl 4-(4-piperidinyl)-1-piperazinecarboxylate bis(trifluoroacetate) salt

생성물 1

HCID 59452755Phenylmethyl4-{1-[2-chloro-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-1-piperazinecarboxylate수율 104.4%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

1-Chloro-2-fluoro-4-(methyloxy)-5-nitrobenzene (2.0 g, 9.7 mmol), from a different batch than previously described, was dissolved in DMSO (50 mL) and K2CO3 (6.7 g, 49 mmol), and phenylmethyl 4-(4-piperidinyl)-1-piperazinecarboxylate bis(trifluoroacetate) salt (5.1 g, 9.7 mmol) were added. Reaction was stirred overnight. Poured into H2O and extracted (2×) with EtOAc. Combined organic layers were back-extracted (5×) with H2O and then dried over MgSO4, filtered, concentrated on to silica gel and flash chromatographed to give the title compound of step C (4.95 g, 100%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.96 (s, 1H), 7.00-7.52 (m, 5H), 6.76 (s, 1H), 5.03 (s, 2H), 3.90 (s, 3H), 3.54 (d, J=12.1 Hz, 2H), 3.17-3.47 (m, 4H), 2.76 (t, J=11.4 Hz, 2H), 2.23-2.63 (m, 5H), 1.82 (d, J=11.5 Hz, 2H), 1.54 (qd, J=11.7, 3.0 Hz, 2H).

후처리

  1. customReaction
  2. extractionextracted (2×) with EtOAc
  3. extractionCombined organic layers were back-extracted (5×) with H2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated on to silica gel and flash
  7. customchromatographed

출처 및 근거

ORD 기록
ord-4fcbb281e66f408ca5ce08eec6bc2b6e
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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