Potassium Iodide → HCID 178429922, compound

HRID 900461Notes

Reaction equation

HRID 900461 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:17]=[C:16]([N:18]3[C:26]4[CH2:25][C:24]([CH3:28])([CH3:27])[CH2:23][C:22](=[O:29])[C:21]=4[C:20]([CH3:30])=[CH:19]3)[CH:15]=[CH:14][C:10]=2[C:11]([NH2:13])=[O:12])[CH2:4][CH2:3]1.Cl.Cl[CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.[H-].[Na+].[I-].[K+]>CN(C=O)C.O>[N:35]1([CH2:34][CH2:33][O:1][C@H:2]2[CH2:7][CH2:6][C@H:5]([NH:8][C:9]3[CH:17]=[C:16]([N:18]4[C:26]5[CH2:25][C:24]([CH3:27])([CH3:28])[CH2:23][C:22](=[O:29])[C:21]=5[C:20]([CH3:30])=[CH:19]4)[CH:15]=[CH:14][C:10]=3[C:11]([NH2:13])=[O:12])[CH2:4][CH2:3]2)[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 178429921HCID 178429921, compound

Product 1

HCID 178429922HCID 178429922, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

A microwave reaction vial was charged with the title compound of Example 3 [2-(trans-4-Hydroxy-cyclohexylamino)-4-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-benzamide] (100 mg, 0.244 mmol), 4-(2-chloroethyl)morpholine hydrochloride (45.4 mg, 0.244 mmol), sodium hydride (17.3 mg, 0.732 mmol), and a catalytic amount of potassium iodide. After suspending in DMF, the reaction mixture was heated to 180° C. in the “Personal Chemistry” microwave for eight minutes. The solution was then diluted with water and extracted into EtOAc (2×). The organic layers were extracted with 2N HCl (2×). The aqueous extracts basified with aqueous sodium hydroxide, and were extracted with EtOAc (3×). The combined organics were dried over Na2SO4, concentrated, and purified by column chromatography (EtOAc/MeOH) to yield the title compounds as a white solid. LCMS m/z: (M+H) 523.9.

Workup

  1. customA microwave reaction
  2. extractionextracted into EtOAc (2×)
  3. extractionThe organic layers were extracted with 2N HCl (2×)
  4. extractionwere extracted with EtOAc (3×)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by column chromatography (EtOAc/MeOH)

Sources & evidence

ORD record
ord-c46d48437ed74d05a6a8993f7a82a6b8
Source dataset
uspto-grants-2008_04
Patent number
US07358370B2

Reaction notes

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