Ethanesulfonyl chloride → HCID 68736610, compound

HRID 1752578Notes

Reaction equation

HRID 1752578 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:12]=[N:13][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:15]=3)[CH:9]=2)[N:4](C(OC(C)(C)C)=O)[N:3]=1.[CH2:30]([S:32](Cl)(=[O:34])=[O:33])[CH3:31].S(Cl)(Cl)(=O)=O>N1C=CC=CC=1>[CH2:16]([N:14]1[CH:15]=[C:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][N:3]=[C:2]3[NH:1][S:32]([CH2:30][CH3:31])(=[O:34])=[O:33])[N:12]=[N:13]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11667Ethanesulfonyl chlorideHCID 24648Sulfuryl chlorideHCID 68737159HCID 68737159, compound

Product 1

HCID 68736610HCID 68736610, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of Example 64A (75 mg, 0.19 mmol) in pyridine (2 mL) was added ethanesulfonyl chloride (25 mg, 0.19 mmol) and the reaction mixture was stirred at room temperature for about 3 hours. Additional sulfonyl chloride (25 mg, 0.19 mmol) was added and the reaction mixture was stirred for about 48 hours. The reaction mixture was concentrated under reduced pressure and the residue dissolved in dichloromethane (10 mL) and washed with 1 N aqueous hydrochloric acid (10 mL). The organic portion was separated, dried under reduced pressure, and treated with hydrochloric acid (4 N in dioxane, 5 mL) and stirred at room temperature for about 12 hours. The reaction mixture was concentrated under reduced pressure and the crude material was purified by reverse-phase HPLC using acetonitrile/water (0.05 M ammonium acetate) gradient elution method to afford the title compound as the acetate salt. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.12 (s, 1H), 8.61 (s, 1H), 8.24 (s, 1H), 7.83 (d, J=8.7 Hz, 1H), 7.52 (d, J=8.7 Hz, 1H), 7.29-7.48 (m, 5H), 5.64 (s, 2H), 3.29 (d, J=9.2 Hz, 2H), 1.31 (t, J=7.3 Hz, 3H). MS (ESI+) m/z 383 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred for about 48 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue dissolved in dichloromethane (10 mL)
  4. washwashed with 1 N aqueous hydrochloric acid (10 mL)
  5. customThe organic portion was separated
  6. customdried under reduced pressure
  7. additiontreated with hydrochloric acid (4 N in dioxane, 5 mL)
  8. stirringstirred at room temperature for about 12 hours
  9. concentrationThe reaction mixture was concentrated under reduced pressure
  10. customthe crude material was purified by reverse-phase
  11. washacetonitrile/water (0.05 M ammonium acetate) gradient elution method

Sources & evidence

ORD record
ord-23d2a9f84b9046bfb4ad4028e8d51143
Source dataset
uspto-grants-2015_10
Patent number
US09163007B2

Reaction notes

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