4-Methylmorpholine → HCID 49847420, compound

HRID 59810Notes

Reaction equation

HRID 59810 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-159a8d47116946de82c9cf9aa6e0341d
Source dataset
uspto-grants-2016_09
Patent number
US09440956B2

Reaction notes

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