Benzoic Acid → HCID 44511300, compound

HRID 42243Notes

Reaction equation

HRID 42243 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:43]1[C:51]2[C:46](=[C:47]([C:52]3[CH:53]=[C:54]([NH2:67])[C:55]4[C:59]([CH:60]=3)=[N:58][N:57](C3CCCCO3)[CH:56]=4)[CH:48]=[CH:49][CH:50]=2)[CH:45]=[CH:44]1>CN(C=O)C>[NH:43]1[C:51]2[C:46](=[C:47]([C:52]3[CH:60]=[C:59]4[C:55]([CH:56]=[N:57][NH:58]4)=[C:54]([NH:67][C:1](=[O:9])[C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:53]=3)[CH:48]=[CH:49][CH:50]=2)[CH:45]=[CH:44]1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582679956-(1H-Indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine

Product 1

HCID 44511300HCID 44511300, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Benzoic acid (10 mg, 0.08 mmol) in DMF (0.2 mL) was treated with HATU (27 mg, 0.07 mmol) in DMF (0.2 mL) and DIPEA (30 μL, 0.24 mmol). The reaction mixture was shaken for five minutes prior to treatment with 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (20 mg, 0.06 mmol) in DMF (0.2 mL). Reaction mixture was shaken for five minutes and left to stand at 22° C. for 18 hrs. Solvent was removed in vacuo and the product re-dissolved in methanol (1 mL) prior to application on to an SCX cartridge (1 g). Product was eluted after 1 hr with 2M ammonia in methanol (2×3 mL), fractions were combined and concentrated under a stream of nitrogen using blow down apparatus. Purification by MDAP (Method D) afforded the title compound.

Workup

  1. customReaction mixture
  2. stirringwas shaken for five minutes
  3. waitleft
  4. waitto stand at 22° C. for 18 hrs
  5. customSolvent was removed in vacuo
  6. dissolutionthe product re-dissolved in methanol (1 mL)
  7. washProduct was eluted after 1 hr with 2M ammonia in methanol (2×3 mL), fractions
  8. concentrationconcentrated under a stream of nitrogen using blow down apparatus
  9. customPurification by MDAP (Method D)

Sources & evidence

ORD record
ord-a94643593c5d4cde8f2ba311aa119a04
Source dataset
uspto-grants-2013_09
Patent number
US08536169B2

Reaction notes

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