8-Quinolinesulfonyl chloride → (R)-4-Allyl-5-(quinolin-8-ylsulfonyl)-3,4,5,6-tetrahydro-1H-benzo[f][1,4]oxazocine

HRID 1429385Notes

Reaction equation

HRID 1429385 reaction equation
[CH2:1]([C@H:4]1[NH:11][CH2:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[CH2:7][O:6][CH2:5]1)[CH:2]=[CH2:3].[N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][C:24]=2[S:26](Cl)(=[O:28])=[O:27])[CH:19]=[CH:18][CH:17]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([C@H:4]1[N:11]([S:26]([C:24]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:25]=2[N:16]=[CH:17][CH:18]=[CH:19]3)(=[O:27])=[O:28])[CH2:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[CH2:7][O:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 292208-Quinolinesulfonyl chlorideHCID 68233282(R)-4-Allyl-3,4,5,6-tetrahydro-1H-benzo[f][1,4]oxazocine

Product 1

HCID 86677162(R)-4-Allyl-5-(quinolin-8-ylsulfonyl)-3,4,5,6-tetrahydro-1H-benzo[f][1,4]oxazocineYield 56%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of compound 18l (1.2 g, 5.9 mmol), quinoline-8-sulfonyl chloride (1.5 g, 6.5 mmol), TEA (1.8 g, 17.7 mmol) and DMAP (366 mg, 3 mmol) in 20 mL of DCM was stirred at rt overnight. The mixture was concentrated and the residue was purified by CC to give the desired compound 18 (1.3 g, 56% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ 8.94 (m, 1H), 8.46 (d, J=7.5 Hz, 1H), 8.13 (d, J=8.5 Hz, 1H), 7.93 (d, J=8.0 Hz, 1H), 7.54 (t, J=8.0 Hz, 1H), 7.43 (dd, J=4.0, 8.0 Hz, 1H), 7.20 (d, J=7.5 Hz, 1H), 6.98 (m, 1H), 6.91 (m, 1H), 6.80 (d, J=7.5 Hz, 1H), 5.69 (m, 1H), 5.07-4.86 (m, 5H), 4.58 (d, J=15.0 Hz, 1H), 4.54 (m, 1H), 4.01 (d, J=12.5 Hz, 1H), 3.68 (d, J=12.5 Hz, 1H), 2.47 (m, 1H), 2.09 (m, 1H). LCMS (m/z): 395.5 (MH+).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by CC

Sources & evidence

ORD record
ord-61714ffbd307479fa2f317e3803eafa6
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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