Diisopropylethylamine → 4-Acetyl-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-morpholinecarboxamide

HRID 42251

Reaction equation

HRID 42251 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([N:28]1[CH2:33][CH2:32][O:31][CH:30]([C:34]([OH:36])=O)[CH2:29]1)(=[O:27])[CH3:26].CCN(C(C)C)C(C)C.[NH:46]1[C:54]2[C:49](=[C:50]([C:55]3[CH:56]=[C:57]([NH2:64])[C:58]4[CH:59]=[N:60][NH:61][C:62]=4[CH:63]=3)[CH:51]=[CH:52][CH:53]=2)[CH:48]=[CH:47]1>CN(C=O)C>[C:25]([N:28]1[CH2:33][CH2:32][O:31][CH:30]([C:34]([NH:64][C:57]2[CH:56]=[C:55]([C:50]3[CH:51]=[CH:52][CH:53]=[C:54]4[C:49]=3[CH:48]=[CH:47][NH:46]4)[CH:63]=[C:62]3[C:58]=2[CH:59]=[N:60][NH:61]3)=[O:36])[CH2:29]1)(=[O:27])[CH3:26]

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 205980784-Acetylmorpholine-2-carboxylic acidHCID 582680196-(1H-indol-4-yl)-1H-indazol-4-amine

Product 1

HCID 445403114-Acetyl-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-morpholinecarboxamideYield 30.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of HATU (0.107 g, 0.28 mmol) in dry DMF (3 ml) was added 4-acetyl-2-morpholinecarboxylic acid (0.05 g, 0.282 mmol). DIPEA (0.098 ml, 0.56 mmol) was added and the mixture was left to stand for 10 min. 6-(1H-indol-4-yl)-1H-indazol-4-amine (0.04 g, 0.14 mmol), dissolved in dry DMF (3 ml) was added and the solution was left to stand at room temperature for 20 hr. DMF was removed by blow down under a stream of nitrogen, then the residue was dissolved and purified by Mass Directed AutoPrep Method B. The solvent was removed in vacuo and product dried in a vacuum oven at 50° C. overnight to give the title compound as a brown oil (17 mg).

Workup

  1. waitthe mixture was left
  2. additionwas added
  3. waitthe solution was left
  4. waitto stand at room temperature for 20 hr
  5. customDMF was removed by blow down under a stream of nitrogen
  6. dissolutionthe residue was dissolved
  7. custompurified by Mass Directed AutoPrep Method B
  8. customThe solvent was removed in vacuo and product
  9. customdried in a vacuum oven at 50° C. overnight

Sources & evidence

ORD record
ord-9c46e66f17024e1990e7244b6b765a50
Source dataset
uspto-grants-2013_09
Patent number
US08536169B2

Linked notes

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