Sodium Iodide → HCID 58379684, compound

HRID 1038991Notes

Reaction equation

HRID 1038991 reaction equation
Cl[CH2:2][C:3]([CH3:38])([CH3:37])[C:4]([N:6]([C@H:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29]1)[CH2:7]/[CH:8]=[CH:9]/[C:10]1[CH:11]=[C:12]2[CH2:27][C@@:17]3([C:25]4[C:20](=[N:21][CH:22]=[CH:23][CH:24]=4)[NH:19][C:18]3=[O:26])[CH2:16][C:13]2=[N:14][CH:15]=1)=[O:5].[Na+].[I-:40]>CC(C)=O>[C@H:28]1([N:6]([CH2:7]/[CH:8]=[CH:9]/[C:10]2[CH:11]=[C:12]3[CH2:27][C@@:17]4([C:25]5[C:20](=[N:21][CH:22]=[CH:23][CH:24]=5)[NH:19][C:18]4=[O:26])[CH2:16][C:13]3=[N:14][CH:15]=2)[C:4](=[O:5])[C:3]([CH3:37])([CH3:38])[CH2:2][I:40])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 58379679HCID 58379679, compound

Product 1

HCID 58379684HCID 58379684, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-chloro-N-[(1R)-2,3-dihydro-1H-inden-1-yl]-2,2-dimethyl-N-{(2E)-3-[(6S)-2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridin]-3-yl]prop-2-en-1-yl}propanamide (120. mg, 0.228 mmol) in acetone (2.3 mL) was added NaI (683 mg, 4.55 mmol). This mixture was heated to 120° C. in a microwave reactor for 30 minutes. After cooling, the bulk of the acetone was removed in vacuo and the residue was partitioned between DCM and water. The organics were dried over sodium sulfate, filtered, and concentrated in vacuo to provide a residue. The residue was then applied to a silica gel column for purification, eluting with a gradient of 1-8% MeOH (containing 10% conc. NH4OH) in DCM to provide the title compound. MS: m/z=619 (M+1).

Workup

  1. temperatureAfter cooling
  2. customthe bulk of the acetone was removed in vacuo
  3. customthe residue was partitioned between DCM and water
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide a residue
  8. customThe residue was then applied to a silica gel column for purification
  9. washeluting with a gradient of 1-8% MeOH (containing 10% conc. NH4OH) in DCM

Sources & evidence

ORD record
ord-8e2a6a266ad24062aec5eb4560ddcb24
Source dataset
uspto-grants-2013_10
Patent number
US08552023B2

Reaction notes

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