Ethanesulfonylchloride, 2-chloro- → HCID 68302610, compound

HRID 1807584Notes

Reaction equation

HRID 1807584 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:12][CH2:11][CH2:10][C:9]2[C:8]([C:13]3[N:17]=[C:16]([C:18]4[CH:19]=[CH:20][C:21]([O:26][CH:27]([CH3:29])[CH3:28])=[C:22]([CH:25]=4)[C:23]#[N:24])[O:15][N:14]=3)=[CH:7][CH:6]=[CH:5][C:4]1=2.Cl[CH2:31][CH2:32][S:33](Cl)(=[O:35])=[O:34]>C(Cl)Cl>[C:23]([C:22]1[CH:25]=[C:18]([C:16]2[O:15][N:14]=[C:13]([C:8]3[CH:7]=[CH:6][CH:5]=[C:4]4[C:9]=3[CH2:10][CH2:11][CH2:12][C@H:3]4[NH:2][S:33]([CH:32]=[CH2:31])(=[O:35])=[O:34])[N:17]=2)[CH:19]=[CH:20][C:21]=1[O:26][CH:27]([CH3:29])[CH3:28])#[N:24]

Participants

4

Reactant 2

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 67198744HCID 67198744, compound

Product 1

HCID 68302610HCID 68302610, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-5-(3-(5-amino-5,6,7,8-tetrahydronaphthalen-1-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile hydrochloride 3 (100 mg, 0.24 mmol) in DCM (5 mL) at 0° C. were added TEA (170 μL, 1.2 mmol) and 2-chloroethanesulfonyl chloride (76 μL, 0.73 mmol). The reaction mixture was warmed to room temperature and stirred for 30 min. The solvent was removed and the product was purified by chromatography (EA/hexane) to give 83.0 mg (75%) of (R)-N-(5-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-1,2,3,4-tetrahydronaphthalen-1-yl)ethenesulfonamide INT-16 as a white solid. LCMS-ESI (m/z) calculated for C24H24N4O4S: 464.5; found 465.1 [M+H]+, tR=3.83 min. 1H NMR (400 MHz, CDCl3) δ 8.41 (d, J=2.2 Hz, 1H), 8.32 (dd, J=8.9, 2.2 Hz, 1H), 7.96 (dd, J=7.7, 1.2 Hz, 1H), 7.62 (t, J=11.0 Hz, 1H), 7.38 (t, J=7.7 Hz, 1H), 7.12 (d, J=9.0 Hz, 1H), 6.66 (dt, J=26.0, 13.0 Hz, 1H), 6.38 (d, J=16.5 Hz, 1H), 6.03 (dd, J=10.1, 5.2 Hz, 1H), 4.86-4.73 (m, 1H), 4.68-4.57 (m, 1H), 4.50 (d, J=8.3 Hz, 1H), 3.18 (dt, J=18.1, 5.8 Hz, 1H), 3.02 (dt, J=18.1, 6.8 Hz, 1H), 2.15-1.96 (m, 2H), 1.97-1.79 (m, 2H), 1.48 (d, J=6.1 Hz, 6H).

Workup

  1. customThe solvent was removed
  2. customthe product was purified by chromatography (EA/hexane)

Sources & evidence

ORD record
ord-05c886f631ab40768f4679e5c18198c0
Source dataset
uspto-grants-2013_01
Patent number
US08357706B2

Reaction notes

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