Triethylamine → HCID 178425365, compound

HRID 642822Notes

Reaction equation

HRID 642822 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18]([C:30]([OH:32])=O)[CH2:19][C:20]3[CH:28]=[C:27]([CH3:29])[C:23]4[NH:24][CH:25]=[N:26][C:22]=4[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:33]=[CH:34][CH:35]=[CH:36][C:4]=2[NH:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[CH2:66]([N:73]1[CH2:78][CH2:77][CH:76]([CH:79]2[CH2:84][CH2:83][NH:82][CH2:81][CH2:80]2)[CH2:75][CH2:74]1)[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.CN(C=O)C>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:19][C:20]3[CH:28]=[C:27]([CH3:29])[C:23]4[NH:24][CH:25]=[N:26][C:22]=4[CH:21]=3)[C:30]([N:82]3[CH2:81][CH2:80][CH:79]([CH:76]4[CH2:75][CH2:74][N:73]([CH2:66][C:67]5[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=5)[CH2:78][CH2:77]4)[CH2:84][CH2:83]3)=[O:32])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:33]=[CH:34][CH:35]=[CH:36][C:4]=2[NH:3]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 337006491-Benzyl-4,4'-bipiperidineHCID 178425374(R)-1-carboxy-2-(7-methyl-1H-benzimidazol-5-yl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Product 1

HCID 178425365HCID 178425365, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 120 mg (0.22 mmol) (R)-1-carboxy-2-(7-methyl-1H-benzimidazol-5-yl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate, 85 mg (0.27 mmol) TBTU and 50 μL (0.36 mmol) triethylamine in 10 mL THF and 1 mL DMF was stirred for 1 h at RT, then combined with 80 mg (0.31 mmol) 1-benzyl-[4,4′]bipiperidinyl and stirred overnight at RT. The reaction solution was combined with 1 mL saturated Na2CO3 solution and extracted with 100 mL EtOAc. The organic phase was dried over Na2SO4, filtered and evaporated down i.vac. The residue was purified via HPLC, the fractions containing the product were combined and evaporated to dryness i.vac.

Workup

  1. extractionextracted with 100 mL EtOAc
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated down i.vac
  5. customThe residue was purified via HPLC
  6. additionthe fractions containing the product
  7. customevaporated to dryness i.vac

Sources & evidence

ORD record
ord-29b124558d3344ab904bfd3ea344d175
Source dataset
uspto-grants-2010_04
Patent number
US07696195B2

Reaction notes

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