4-Methylmorpholine → HCID 49847420, compound

HRID 446231Notes

Reaction equation

HRID 446231 reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[C:8]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=3)[CH:9]=[C:10]([C:13]([OH:15])=O)[CH:11]=2)[CH:6]=[N:5]1)([CH3:3])[CH3:2].[CH3:23][C:24]1[N:25]=[CH:26][C:27]([CH2:30][NH2:31])=[N:28][CH:29]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(#N)C>[CH3:23][C:24]1[N:25]=[CH:26][C:27]([CH2:30][NH:31][C:13]([C:10]2[CH:11]=[C:12]3[C:7]([CH:6]=[N:5][N:4]3[CH:1]([CH3:2])[CH3:3])=[C:8]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=3)[CH:9]=2)=[O:15])=[N:28][CH:29]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27564962-(Aminomethyl)-5-methylpyrazineHCID 596277631-isopropyl-4-(5-methyl-pyridin-2-yl)-1H-indazole-6-carboxylic acid

Product 1

HCID 49847420HCID 49847420, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-isopropyl-4-(5-methyl-pyridin-2-yl)-1H-indazole-6-carboxylic acid (0.24 g, 0.814 mmol) in acetonitril was added C-(5-methyl-pyrazin-2-yl)-methylamine (0.12 g, 0.976 mmol), EDCI (0.23 g, 1.22 mmol), HOBt (0.16 g, 1.22 mmol), and NMM (0.45 mL, 4.07 mmol). The reaction mixture was stirred at room temperature overnight, then partitioned between water and ethyl acetate. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by column chromatography gave 0.144 g (44%) of 1-isopropyl-4-(5-methyl-pyridin-2-yl)-1H-indazole-6-carboxylic acid (5-methyl-pyrazin-2-ylmethyl)-amide MS (M+H)=401.

Workup

  1. custompartitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by column chromatography

Sources & evidence

ORD record
ord-b748a1944aa74398a7da5b3b46a0e919
Source dataset
uspto-grants-2013_07
Patent number
US08476457B2

Reaction notes

Loading…