1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178522777, compound

HRID 2059731Notes

Reaction equation

HRID 2059731 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][C:8]([C:10](=[CH:15]N(C)C)[C:11](OC)=[O:12])=[O:9])=[CH:4][CH:3]=1.Cl.[N:22]1([C:27](=[NH:29])[NH2:28])[CH:26]=[CH:25][CH:24]=[N:23]1.C1CCN2C(=NCCC2)CC1>CC(N(C)C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:12])=[N:29][C:27]([N:22]3[CH:26]=[CH:25][CH:24]=[N:23]3)=[N:28][CH:15]=2)=[O:9])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 69079036HCID 69079036, compound

Product 1

HCID 178522777HCID 178522777, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

All of the unpurified product of step B was diluted with DMA (28 mL) before adding 1H-pyrazole-1-carboximidamide hydrochloride (5.13 g, 35.0 mmol), and DBU (5.28 mL, 35.0 mmol) at rt. The reaction was aged at 110° C. for about 30 min. The reaction was diluted with EtOAc and washed with aq. 2 M HCl and water. The organic portion was concentrated and diluted with EtOH. The mixture was aged for about 30 min at 75° C. and cooled. The solid is isolated by filtration and washed with EtOH to afford the title compound. HPLC/MS: 374.0 (M+1); Rt=2.70 min.

Workup

  1. washwashed with aq. 2 M HCl and water
  2. concentrationThe organic portion was concentrated
  3. additiondiluted with EtOH
  4. waitThe mixture was aged for about 30 min at 75° C.
  5. temperaturecooled
  6. customThe solid is isolated by filtration
  7. washwashed with EtOH

Sources & evidence

ORD record
ord-6198ea036acd4210b0b5594d7035ab37
Source dataset
uspto-grants-2012_10
Patent number
US08278304B2

Reaction notes

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