Diisopropylethylamine → HCID 44540867, compound

HRID 1616009Notes

Reaction equation

HRID 1616009 reaction equation
[CH3:1][S:2]([C:5]1[C:6]([C:11]([OH:13])=O)=[N:7][CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[NH:47]1[C:55]2[C:50](=[C:51]([C:56]3[CH:57]=[C:58]([NH2:65])[C:59]4[CH:60]=[N:61][NH:62][C:63]=4[CH:64]=3)[CH:52]=[CH:53][CH:54]=2)[CH:49]=[CH:48]1>CN(C=O)C>[NH:47]1[C:55]2[C:50](=[C:51]([C:56]3[CH:64]=[C:63]4[C:59]([CH:60]=[N:61][NH:62]4)=[C:58]([NH:65][C:11]([C:6]4[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=[CH:8][N:7]=4)=[O:13])[CH:57]=3)[CH:52]=[CH:53][CH:54]=2)[CH:49]=[CH:48]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 123612403-(Methanesulfonyl)pyridine-2-carboxylic acidHCID 582680196-(1H-indol-4-yl)-1H-indazol-4-amine

Product 1

HCID 44540867HCID 44540867, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To 3-(methylsulfonyl)-2-pyridinecarboxylic acid (which may be prepared as described by Blank, Benjamin; DiTullio, Nicholas W.; Owings, Franklin F.; Deviney, Linda; Miao, Clara K.; Saunders, Harry L. Journal of Medicinal Chemistry (1977), 20(4), 572-576.) (89 mg, 0.44 mmol) was added O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (172 mg, 0.45 mmol), DIPEA (0.106 ml) and DMF (1 ml). The reaction was stirred for 20 mins at 25° C. 6-(1H-Indol-4-yl)-1H-indazol-4-amine (50 mg, 0.20 mmol) was added and the reaction was stirred for a further 20 h at 25° C. The solvent was dried under a stream of nitrogen to give the crude product. This sample in DMF was loaded onto an aminopropyl cartridge (5 g) and after standing for 3 h, the column was washed with 10% methanol in dichloromethane. The appropriate fractions were combined and dried under a stream of nitrogen to give the crude product which was purified by Mass Directed Automated Preparative HPLC (Method B). The solvent was dried under a stream of nitrogen to give the title compound (29 mg).

Workup

  1. stirringthe reaction was stirred for a further 20 h at 25° C
  2. customThe solvent was dried under a stream of nitrogen
  3. customto give the crude product
  4. waitafter standing for 3 h
  5. washthe column was washed with 10% methanol in dichloromethane
  6. customdried under a stream of nitrogen
  7. customto give the crude product which
  8. customwas purified by Mass Directed Automated Preparative HPLC (Method B)
  9. customThe solvent was dried under a stream of nitrogen

Sources & evidence

ORD record
ord-2199023e3b44420cbee249046dcadbea
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

Loading…