Benzenesulfonyl chloride → (S)-N-(6-Cyano-1,2,3,4-tetrahydro-quinolin-3-yl)-benzenesulfonamide

HRID 1643863Notes

Reaction equation

HRID 1643863 reaction equation
[NH2:1][C@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]#[N:13])[CH:9]=2)[NH:4][CH2:3]1.CCN(C(C)C)C(C)C.[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CC#N>[C:12]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][CH2:3][C@@H:2]([NH:1][S:29]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:31])=[O:30])[CH2:11]2)#[N:13]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66757521(S)-3-Amino-1,2,3,4-tetrahydroquinoline-6-carbonitrile

Product 1

HCID 66757946(S)-N-(6-Cyano-1,2,3,4-tetrahydro-quinolin-3-yl)-benzenesulfonamideYield 90.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1F (103.9 mg, 0.6 mmol) in CH3CN (3 mL) at RT under argon was added DIPEA (0.11 mL, 0.66 mmol), followed by dropwise addition of benzene sulfonylchloride (0.08 mL, 0.63 mmol). The reaction mixture was stirred at RT for 1.5 h, then concentrated under reduced pressure. The residue was taken into EtOAc, washed with water, brine, dried (Na2SO4), and concentrated. The resulting residue was chromatographed (silica gel) eluting with EtOAc (30-50%) in hexane to give the title compound (170 mg, 90%). HPLC: 99% at 5.2 min (retention time) (Conditions: Zorbax SB C18 (4.6×75 mm); Eluted with 0% to 100% B, 8 min gradient. (A=90% H2O−10% MeOH−0.1% H3PO4 and B=10% H2O−90% MeOH−0.1% H3PO4); Flow rate at 2.5 mL/min. UV detection at 220 nm). MS (ES): m/z 314 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed with water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe resulting residue was chromatographed (silica gel)
  6. washeluting with EtOAc (30-50%) in hexane

Sources & evidence

ORD record
ord-bed0810734e64f1cbb384b55557fdabe
Source dataset
uspto-grants-2012_02
Patent number
US08119808B2

Reaction notes

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