Potassium Iodide → HCID 72189888, compound

HRID 1487047Notes

Reaction equation

HRID 1487047 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=2[CH3:24])[CH2:13][CH:14]([CH3:16])[CH3:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[O:25]1[CH2:30][CH2:29][CH:28]([CH2:31]O)[CH2:27][CH2:26]1.[I-].[K+]>O>[CH3:24][C:18]1[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=1[N:12]([CH2:13][CH:14]([CH3:16])[CH3:15])[S:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][NH:1][CH2:31][CH:28]2[CH2:29][CH2:30][O:25][CH2:26][CH2:27]2)=[CH:4][CH:5]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 2773573(Oxan-4-yl)methanol2×HCID 117952993HCID 117952993, compound

Product 1

HCID 72189888HCID 72189888, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

4-(aminomethyl)-N-(2,4-dimethylphenyl)-N-isobutylbenzenesulfonamide (25 mg, 0.072 mmol), (tetrahydro-2H-pyran-4-yl)methanol (16.76 mg, 0.144 mmol), potassium iodide (23.95 mg, 0.144 mmol) and [Cp*IrCl2]2 (1.150 mg, 1.443 μmol) were dissolved in water (2 mL) in a microwave vial. The reaction vessel was sealed and heated by microwaves (Biotage Initiator) to 150° C. for 1 hour. After analysis the reaction vessel was resealed and heated again by microwaves (Biotage Initiator) to 150° C. for a further 1 hour. After further analysis an additional 1 eq of [Cp*IrCl2]2 and 1 eq of (tetrahydro-2H-pyran-4-yl)methanol were added and the reaction heated for a third time by microwaves (Biotage Initiator) to 150° C. for 1 hour. The reaction was cooled and the mixture concentrated in vacuo (Biotage V10). The crude product was extracted to the organic phase of an aqueous workup between ethyl acetate (5 mL) and water (5 mL). The organic phase was passed through a hydrophobic frit and concentrated in vacuo. The crude was purified by mass directed autoprep (formic acid modifier). The appropriate fractions were evaporated in vacuo (Biotage V10) to give the required product, 1.2 mg. LCMS [LCMS1] Rt 0.97 min, m/z (ES+) 445 (M+H).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureheated again by microwaves (Biotage Initiator) to 150° C. for a further 1 hour
  3. temperaturethe reaction heated for a third time by microwaves (Biotage Initiator) to 150° C. for 1 hour
  4. temperatureThe reaction was cooled
  5. concentrationthe mixture concentrated in vacuo (Biotage V10)
  6. extractionThe crude product was extracted to the organic phase of an aqueous workup between ethyl acetate (5 mL) and water (5 mL)
  7. concentrationconcentrated in vacuo
  8. customThe crude was purified by mass
  9. customThe appropriate fractions were evaporated in vacuo (Biotage V10)

Sources & evidence

ORD record
ord-b345e5de3e7b4a5c88a6fd97b1e92bd3
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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