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Tetrahydrofuran → HCID 9853348, compound

HRID 323326
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Reaction equation

HRID 323326 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:39]=[C:40]([O:44][CH3:45])[C:41]=1[O:42][CH3:43])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH:29][C:30]3[NH:34][C:33]4[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=4[N:31]=3)[CH2:25][CH2:24]2)([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[CH2:9]1)=[O:7].O1CCCC1.C([Li])(CC)C.CS(O[CH2:61][CH2:62][S:63]([CH3:66])(=[O:65])=[O:64])(=O)=O>CO.O>[CH3:45][O:44][C:40]1[CH:39]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:41]=1[O:42][CH3:43])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH:29][C:30]3[N:31]([CH2:61][CH2:62][S:63]([CH3:66])(=[O:65])=[O:64])[C:32]4[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=4[N:34]=3)[CH2:25][CH2:24]2)([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[CH2:9]1)=[O:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 184645972-(Methylsulfonyl)ethyl methanesulfonateHCID 220092161-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-difluorophenyl)pyrrolidineHCID 178418400CID 53628100

Product 1

HCID 9853348HCID 9853348, compound

Reagents, catalysts & solvents

2
HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-difluorophenyl)pyrrolidine (1.51 g, 2.44 mmol) and tetrahydrofuran (20 mL). Cool to −78° C. using a dry-ice/acetone bath. Add a solution of s-butyl lithium (3.94 mL, 1.3 M in hexane, 5.12 mmol). After 30 minutes, add a solution of 2-methylsulfonylethyl methanesulfonate (0.60 g, 2.93 mmol). Allow to warm to ambient temperature and then heat to reflux. After 48 hours, cool to ambient temperature and add water. Separate the layers. Extract the aqueous layer four times with ethyl acetate. Combine the organic layers, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 5/0.5/94.5 methanol/concentrated ammonium hydroxide/dichloromethane to give the title compound: Rf=0.54 (silica gel, 5/0.5/94.5 methanol/concentrated ammonium hydroxide/dichloromethane).

Workup

  1. temperatureAllow to warm to ambient temperature
  2. temperatureheat to reflux
  3. waitAfter 48 hours
  4. temperaturecool to ambient temperature
  5. customSeparate the layers
  6. extractionExtract the aqueous layer four times with ethyl acetate
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a residue

Sources & evidence

ORD record
ord-e945841010a94fa7bb5999284a8f4b6c
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211199B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes