Diisopropylethylamine → HCID 44540315, compound

HRID 1616045Notes

Reaction equation

HRID 1616045 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=[CH:5][N:4]=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:45]1[C:53]2[C:48](=[C:49]([C:54]3[CH:55]=[C:56]([NH2:63])[C:57]4[CH:58]=[N:59][NH:60][C:61]=4[CH:62]=3)[CH:50]=[CH:51][CH:52]=2)[CH:47]=[CH:46]1>CN(C=O)C>[NH:45]1[C:53]2[C:48](=[C:49]([C:54]3[CH:62]=[C:61]4[C:57]([CH:58]=[N:59][NH:60]4)=[C:56]([NH:63][C:9]([C:8]4[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=4)=[O:11])[CH:55]=3)[CH:50]=[CH:51][CH:52]=2)[CH:47]=[CH:46]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 7080932-Methoxynicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582680196-(1H-indol-4-yl)-1H-indazol-4-amine

Product 1

HCID 44540315HCID 44540315, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-(Methyloxy)-3-pyridinecarboxylic acid (33 mg, 0.22 mmol) was treated with HATU (84 mg, 0.22 mmol) in DMF (0.25 ml) and DIPEA (0.069 ml, 0.40 mmol). The reaction mixture was shaken for 5 mins prior to treatment with 6-(1H-indol-4-yl)-1H-indazol-4-amine (25 mg, 0.1 mmol) in DMF (0.25 ml) and then left to stand at room temperature for 18 h. Solvent was removed in vacuo and the product re-dissolved in chloroform (0.3 ml) prior to application on to a pre-conditioned (methanol then chloroform) aminopropyl SPE cartridge (0.5 g). Product was eluted after 2 h with ethyl acetate/methanol (1:1, 3 ml), and concentrated under a stream of nitrogen using blow down apparatus. Purification by MDAP(Method D) afforded the title compound (2 mg).

Workup

  1. waitto stand at room temperature for 18 h
  2. customSolvent was removed in vacuo
  3. dissolutionthe product re-dissolved in chloroform (0.3 ml)
  4. washProduct was eluted after 2 h with ethyl acetate/methanol (1:1, 3 ml)
  5. concentrationconcentrated under a stream of nitrogen using blow down apparatus
  6. customPurification by MDAP(Method D)

Sources & evidence

ORD record
ord-9cfdb77f861743719c8ff54dab69e1da
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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