Triethylamine → HCID 178425368, compound

HRID 642824Notes

Reaction equation

HRID 642824 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](O)=[O:31])[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][N: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+]>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[CH2:83][CH2:84][CH:79]([N:76]4[CH2:75][CH2:74][N:73]([CH2:66][C:67]5[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=5)[CH2:78][CH2:77]4)[CH2:80][CH2:81]3)=[O:31])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:36]2[CH:35]=[CH:34][CH:33]=[CH:5][C:4]=2[NH:3]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 36792751-Benzyl-4-piperidin-4-yl-piperazineHCID 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 178425368HCID 178425368, 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 120 μL (0.86 mmol) triethylamine in 10 mL THF and 1 mL DMF was stirred for 1 h at RT, then combined with 90 mg (0.27 mmol) 1-benzyl-4-piperidin-4-yl-piperazine (used as the bishydrochloride salt) and stirred overnight at RT. The reaction solution was combined with 1 mL semisaturated NaHCO3 solution and extracted with 100 mL EtOAc. The organic phase was dried over Na2SO4, filtered and evaporated down 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

Sources & evidence

ORD record
ord-75f4b599e5a540b88b90c16335794eb9
Source dataset
uspto-grants-2010_04
Patent number
US07696195B2

Reaction notes

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