Hydrochloric Acid → HCID 69512979, compound

HRID 1272723Notes

Reaction equation

HRID 1272723 reaction equation
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=[N:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:25]1([NH:28][C:29]([C:31]2[CH:32]=[C:33]([C:43]([CH3:46])=[CH:44][CH:45]=2)[C:34]2C=CC(C(O)=O)=[CH:36][CH:35]=2)=[O:30])[CH2:27][CH2:26]1.C1C=CC2N([OH:56])N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.CN([CH:70]=[O:71])C>C(OCC)(=O)C>[CH:25]1([NH:28][C:29]([C:31]2[CH:32]=[C:33]([C:34]3[CH:11]=[CH:12][C:13]([C:14]([NH:15][CH2:10][CH2:70][OH:71])=[O:56])=[CH:36][CH:35]=3)[C:43]([CH3:46])=[CH:44][CH:45]=2)=[O:30])[CH2:26][CH2:27]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 112201515′-[(Cyclopropylamino)carbonyl]-2′-methyl[1,1′-biphenyl]-4-carboxylic acid

Product 1

HCID 69512979HCID 69512979, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

HATU (65 mg, 0.17 mmol) was added to a solution of {3′-[(cyclopropylamino)carbonyl]-6′-methyl-biphen-4-yl} carboxylic acid (50 mg, 0.17 mmol) in DMF (2 ml). After 5 minutes HOBT (23 mg, 0.17 mmol), amine (0.17 mmol) and DIPEA (0.087 ml, 0.51 mmol) were added and the reaction mixture stirred at room temperature under nitrogen for 18 hours. Ethyl acetate (50 ml) and hydrochloric acid (1M, 50 ml) were added and the layers separated. The organic layer was washed with aqueous sodium carbonate (1M, 50 ml), brine (25 ml), dried (magnesium sulphate) and solvent removed in vacuo. The crude material was purified by SPE cartridge (Si, 5 g) eluting with DCM:ethanol:ammonia 400:8:1, then, ethyl acetate, acetonitrile, acetone and ethanol to yield the desired product.

Workup

  1. customthe layers separated
  2. washThe organic layer was washed with aqueous sodium carbonate (1M, 50 ml), brine (25 ml)
  3. dry with materialdried (magnesium sulphate) and solvent
  4. customremoved in vacuo
  5. customThe crude material was purified by SPE cartridge (Si, 5 g)
  6. washeluting with DCM:ethanol:ammonia 400:8:1

Sources & evidence

ORD record
ord-478982feed204563a96aa9fbd2aa8bfc
Source dataset
uspto-grants-2007_04
Patent number
US07208629B2

Reaction notes

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