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Sodium hydride → 1-t-butoxycarbonyl-4-(1-(4,4,4-trifluorobutyl)-1H-benzimidazol-2-yl)[1,4]diazepane

HRID 1584478
Notes
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Reaction equation

HRID 1584478 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH2:27][CH2:28][CH2:29][C:30]([F:33])([F:32])[F:31].[Cl-].[NH4+]>O1CCCC1.CN(C)C=O.C(OCC)(=O)C.CCCCCC>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:16]([CH2:27][CH2:28][CH2:29][C:30]([F:33])([F:32])[F:31])[C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27751891,1,1-Trifluoro-4-iodobutaneHCID 184646551-t-butoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane

Product 1

HCID 212236081-t-butoxycarbonyl-4-(1-(4,4,4-trifluorobutyl)-1H-benzimidazol-2-yl)[1,4]diazepane

Reagents, catalysts & solvents 3

HCID 6228
Dimethylformamide
Solvent
HCID 8028TetrahydrofuranSolvent
HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine 1-t-butoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane (1.5 g, 4.74 mmol) in tetrahydrofuran (45 mL) and dimethylformamide (5 mL). Cool in an ice bath. Add sodium hydride (0.23 g, 60% in oil, 5.7 mmol). Warm to ambient temperature. After about 90 minutes, when the gas evolution ceases, add 1-iodo-4,4,4-trifluorobutane (1.35 g, 5.7 mmol). After 18 hours, add ice and then a saturated aqueous solution of ammonium chloride. Evaporate the reaction mixture to remove most of the tetrahydrofuran, dilute with ethyl acetate and extract with water and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 60% ethyl acetate/hexane to give 1-t-butoxycarbonyl-4-(1-(4,4,4-trifluorobutyl)-1H-benzimidazol-2-yl)[1,4]diazepane: Rf =0.40 (silica gel, ethyl acetate).

Workup

  1. temperatureCool in an ice bath
  2. waitAfter 18 hours
  3. additionadd ice
  4. customEvaporate the reaction mixture
  5. customto remove most of the tetrahydrofuran
  6. additiondilute with ethyl acetate
  7. extractionextract with water
  8. dry with materialDry the organic layer over MgSO4
  9. filtrationfilter
  10. customevaporate in vacuo
  11. customto give a residue

Sources & evidence

ORD record
ord-2ea7bcc5931b420bbd68169d7c70a9ef
Source dataset
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05932571

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes