8-Quinolinesulfonyl chloride → HCID 68233375, compound

HRID 1429372Notes

Reaction equation

HRID 1429372 reaction equation
[C:1]([O:5][CH2:6][C@H:7]1[NH:14][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[CH2:10][O:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[S:29](Cl)(=[O:31])=[O:30])[CH:22]=[CH:21][CH:20]=1>N1C=CC=CC=1>[C:1]([O:5][CH2:6][C@H:7]1[N:14]([S:29]([C:27]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:28]=2[N:19]=[CH:20][CH:21]=[CH:22]3)(=[O:30])=[O:31])[CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[CH2:10][O:9][CH2:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 292208-Quinolinesulfonyl chlorideHCID 68233579HCID 68233579, compound

Product 1

HCID 68233375HCID 68233375, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of compound 14f (crude, 129 mg, 0.5 mmol) in pyridine (4 mL) at rt was added quinoline-8-sulfonyl chloride (142 mg, 0.6 mmol). The reaction mixture was stirred for 16 h and concentrated under reduced pressure. The residue was partitioned between CHCl3 and H2O. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by Prep-TLC to give compound 14 (100 mg, 44% yield). 1H NMR (400 MHz, CDCl3) δ 8.97 (s, 1H), 8.49 (d, 1H, J=8.0 Hz), 8.17 (d, 1H, J=8.0 Hz), 7.97 (d, 1H, J=8.0 Hz), 7.56 (t, 1H, J=8.0 Hz), 7.47-7.44 (m, 1H), 7.21 (d, 1H, J=8.0 Hz), 7.02-7.00 (m, 1H), 6.94-6.93 (m, 1H), 6.87 (d, 1H, J=8.0 Hz), 5.17 (d, 1H, J=8.0 Hz), 4.98-4.93 (m, 2H), 4.66 (d, 1H, J=8.0 Hz), 4.51 (s, 1H), 4.27 (d, 1H, J=8.0 Hz), 3.78 (d, 1H, J=8.0 Hz), 3.53 (t, 1H, J=7.2 Hz), 3.21-3.18 (m, 1H), 1.00 (s, 9H). MS (ESI) calcd for [C24H28N2O4S+H]+ (m/z): 441.56. found: 441.3.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between CHCl3 and H2O
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by Prep-TLC

Sources & evidence

ORD record
ord-c2479318932042a48a88f6691e7479eb
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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