Acetonitrile → HCID 89777805, compound

HRID 1752532Notes

Reaction equation

HRID 1752532 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]([NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:14].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:30][CH2:31][N:32]1[CH2:37][C@H:36]([CH3:38])[O:35][C@H:34]([CH3:39])[CH2:33]1.CC#N>CC(C)=O>[CH3:39][C@H:34]1[O:35][C@@H:36]([CH3:38])[CH2:37][N:32]([CH2:31][CH2:30][N:20]2[CH2:21][CH2:22][CH:17]([CH2:16][NH:15][C:13]([C:7]3[C:6]4[C:10](=[CH:11][CH:12]=[C:4]([O:3][CH3:2])[CH:5]=4)[NH:9][N:8]=3)=[O:14])[CH2:18][CH2:19]2)[CH2:33]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 53215608HCID 53215608, compoundHCID 89767058HCID 89767058, compound

Product 1

HCID 89777805HCID 89777805, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of compound 7b (8 g, 24.6 mmoles) and potassium carbonate (17 g, 123 mmoles) in acetone (250 mL) was refluxed for 1 hour, then (2R,6S)-4-(2-chloroethyl)-2,6-di methyl morpholine (25.9 mmoles) was added dropwise. The mixture was refluxed overnight then was cooled and filtered. The resulting solid was dried and purified via preparative HPLC (channel A=CH3CN+0.1% formic acid; channel B=H2O+0.1% formic acid: flow=40 ml/min; gradient=10%-45% of eluent A in 15 minutes) providing N-[(1-{2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl}piperidin-4-yl)methyl]-5-methoxy-1H-indazole-3-carboxamide 25 (48.3% yield)

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureThe mixture was refluxed overnight
  3. temperaturethen was cooled
  4. filtrationfiltered
  5. customThe resulting solid was dried
  6. custompurified via preparative HPLC (channel A=CH3CN+0.1% formic acid

Sources & evidence

ORD record
ord-b0a4cca2d805433ab2ffb0ff6d90fd97
Source dataset
uspto-grants-2015_10
Patent number
US09163013B2

Reaction notes

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