Acetonitrile → HCID 178457835, 화합물

HRID 518672

반응식

HRID 518672 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([N+:22]([O-:24])=[O:23])=[C:7]([NH:9][C@@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]([NH:18][CH:19]([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH:8]=1.S(Cl)(Cl)=O.C(#N)C.[NH:32]1[CH2:37][CH2:36][CH:35]([C:38]([OH:41])([CH3:40])[CH3:39])[CH2:34][CH2:33]1>C(Cl)Cl.CO>[NH4+:9].[OH-:1].[OH:41][C:38]([CH:35]1[CH2:36][CH2:37][N:32]([CH2:2][C:3]2[CH:4]=[CH:5][C:6]([N+:22]([O-:24])=[O:23])=[C:7]([NH:9][C@@H:10]3[CH2:11][CH2:12][C@H:13]([C:16]([NH:18][CH:19]([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]3)[CH:8]=2)[CH2:33][CH2:34]1)([CH3:40])[CH3:39]

참가 물질

8

반응물 4

HCID 6342AcetonitrileHCID 24386Thionyl ChlorideHCID 52003212-(4-Piperidyl)-2-propanolHCID 178457837HCID 178457837, 화합물

생성물 2

HCID 14923Ammonium HydroxideHCID 178457835HCID 178457835, 화합물수율 180.1%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of cis-4-(5-(hydroxymethyl)-2-nitrophenylamino)-N-isopropylcyclohexanecarboxamide (3.75 g, 11.18 mmol) in DCM (127 mL) at 0° C. was added thionyl chloride (4.08 mL, 55.9 mmol) dropwise. The reaction was stirred at 0° C. for 3 hours and then at RT for 2 hours. The reaction was concentrated in vacuo and suspended in ACN and re-concentrated to remove residual thionyl chloride. The residue was resuspended in ACN (102 mL, 11.18 mmol), cooled to 0° C., and to it was added 2-(piperidin-4-yl)propan-2-ol (5.60 g, 39.1 mmol). The reaction was stirred at RT overnight. The mixture was filtered, and the filtrate concentrated in vacuo. The residual material was purified via silica gel chromatography, eluting with 90:10:1 DCM:MeOH:NH4OH to provide cis-4-(5-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-2-nitrophenylamino)-N-isopropylcyclohexanecarboxamide (4.64 g, 10.07 mmol, 90% yield) as an orange solid. MS m/z=461.4 [M+H], calc 460.61 for C25H40N4O4.

후처리

  1. waitat RT for 2 hours
  2. concentrationThe reaction was concentrated in vacuo
  3. concentrationre-concentrated
  4. customto remove residual thionyl chloride
  5. temperaturecooled to 0° C.
  6. stirringThe reaction was stirred at RT overnight
  7. filtrationThe mixture was filtered
  8. concentrationthe filtrate concentrated in vacuo
  9. customThe residual material was purified via silica gel chromatography
  10. washeluting with 90:10:1 DCM

출처 및 근거

ORD 기록
ord-c3cf6107a4c94976af1aae35b8a24af8
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115127B2

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