Diisopropylethylamine → [4-(3,4-Dichloro-phenoxy)-[1,4']bipiperidinyl-1'-yl]-(3-methanesulfonyl-phenyl)-methanone acetate

HRID 349738노트

반응식

HRID 349738 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH2:8][CH2:7]1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.[CH3:46][S:47]([C:50]1[CH:51]=[C:52]([CH:56]=[CH:57][CH:58]=1)[C:53]([OH:55])=[O:54])(=[O:49])=[O:48].C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>C1COCC1.C(OCC)(=O)C>[C:53]([OH:55])(=[O:54])[CH3:52].[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH:12]2[CH2:13][CH2:14][N:15]([C:53]([C:52]3[CH:56]=[CH:57][CH:58]=[C:50]([S:47]([CH3:46])(=[O:49])=[O:48])[CH:51]=3)=[O:54])[CH2:16][CH2:17]2)[CH2:10][CH2:11]1

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 2203803-Methanesulfonylbenzoic acidHCID 516892Sodium BicarbonateHCID 2733179PyBroPHCID 223974344-(3,4-Dichloro-phenoxy)-[1,4']bipiperidine

생성물 1

HCID 22397435[4-(3,4-Dichloro-phenoxy)-[1,4']bipiperidinyl-1'-yl]-(3-methanesulfonyl-phenyl)-methanone acetate수율 73.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

The product of Step b (0.15 g) was dissolved in THF (4 ml), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PYBROP™; 0.235 g), 3-methylsulphonylbenzoic acid (0.091 g) and N,N-di-iso-propylethylamine (0.238 ml) were added. After 18 hours at room temperature ethyl acetate and aqueous NaHCO3 solution were added. The product was extracted with ethyl acetate, the combined organic extracts dried with Na2SO4 and concentrated. Purification by reverse phase HPLC (with a gradient eluent system (45% MeCN/NH4OAcaq (0.1%) to 95% MeCN//NH4OAcaq (0.1%)) gave the title compound (0.095 g).

후처리

  1. extractionThe product was extracted with ethyl acetate
  2. dry with materialthe combined organic extracts dried with Na2SO4
  3. concentrationconcentrated
  4. customPurification by reverse phase HPLC (with a gradient eluent system (45% MeCN/NH4OAcaq (0.1%) to 95% MeCN//NH4OAcaq (0.1%))

출처 및 근거

ORD 기록
ord-852a4365485b4ef1b25beff85a327c49
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179922B2

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