Triethylamine → HCID 16124532, compound

HRID 730649Notes

Reaction equation

HRID 730649 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[O:13]=[C:14]1[N:20]([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C@@H:30]([C:41](O)=[O:42])[CH2:31][C:32]3[CH:37]=[C:36]([CH3:38])[C:35]([OH:39])=[C:34]([CH3:40])[CH:33]=3)=[O:28])[CH2:23][CH2:22]2)[CH2:19][CH2:18][C:17]2[CH:44]=[CH:45][CH:46]=[CH:47][C:16]=2[NH:15]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>C1COCC1.CN(C=O)C.CCOC(C)=O>[O:13]=[C:14]1[N:20]([CH:21]2[CH2:22][CH2:23][N:24]([C:27]([O:29][C@H:30]([CH2:31][C:32]3[CH:33]=[C:34]([CH3:40])[C:35]([OH:39])=[C:36]([CH3:38])[CH:37]=3)[C:41](=[O:42])[N:10]3[CH2:9][CH2:8][CH:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)[CH2:12][CH2:11]3)=[O:28])[CH2:25][CH2:26]2)[CH2:19][CH2:18][C:17]2[CH:44]=[CH:45][CH:46]=[CH:47][C:16]=2[NH:15]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11395974-(4-Piperidyl)pyridineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67273812HCID 67273812, compound

Product 1

HCID 16124532HCID 16124532, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

67 mg (0.42 mmol) 1,2,3,4,5,6-hexahydro-[4,4′]bipyridinyl were added at RT to a solution of 182 mg (0.38 mmol) (R)-2-(4-hydroxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate, 133 mg (0.42 mmol) TBTU and 66 μL (0.47 mmol) triethylamine in 10 mL THF and 2 mL DMF and the reaction mixture was stirred for 2 h. 20 mL EtOAc were added, the organic phase was washed with 20 mL semisaturated NaHCO3 solution and dried on Na2SO4. After the elimination of the desiccant and solvent the residue was purified by HPLC. The fractions containing the product were combined, evaporated down, the residue was made alkaline with semisaturated NaHCO3 solution, extracted with 50 mL EtOAc and the organic phase was dried on Na2SO4. After the elimination of the desiccant and solvent the residue was stirred with DIPE, suction filtered and dried.

Workup

  1. washthe organic phase was washed with 20 mL
  2. customdried on Na2SO4
  3. customAfter the elimination of the desiccant and solvent the residue was purified by HPLC
  4. additionThe fractions containing the product
  5. customevaporated down
  6. extractionextracted with 50 mL EtOAc
  7. customthe organic phase was dried on Na2SO4
  8. stirringAfter the elimination of the desiccant and solvent the residue was stirred with DIPE, suction
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-1b99022aa9da4df8b5cd4ece1131acf1
Source dataset
uspto-grants-2009_09
Patent number
US07582625B2

Reaction notes

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