6-Methoxy-m-toluenesulfonyl chloride → HCID 66893379, compound

HRID 1161994Notes

Reaction equation

HRID 1161994 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[O:19])[CH2:13][CH2:12]2)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:28]=1[S:34]([Cl:37])(=[O:36])=[O:35].ClC1C=CC=CC=1S(NC1C=C(N2CCN(C(OC(C)(C)C)=O)CC2)C2OC=CC=2C=1)(=O)=O>CC#N>[ClH:37].[CH2:21]([N:20]([CH2:23][CH3:24])[C:18](=[O:19])[CH2:17][N:14]1[CH2:15][CH2:16][N:11]([C:4]2[C:5]3[O:9][CH:8]=[CH:7][C:6]=3[CH:10]=[C:2]([NH:1][S:34]([C:28]3[CH:29]=[C:30]([CH3:33])[CH:31]=[CH:32][C:27]=3[O:26][CH3:25])(=[O:36])=[O:35])[CH:3]=2)[CH2:12][CH2:13]1)[CH3:22]

Participants

5

Reactant 3

HCID 1451496-Methoxy-m-toluenesulfonyl chlorideHCID 66894206HCID 66894206, compound2×HCID 69630494HCID 69630494, compound

Product 1

HCID 66893379HCID 66893379, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-[4-(5-Amino-1-benzofuran-7-yl)piperazin-1-yl]-N,N-diethylacetamide (0.095 g, 0.29 mmol; Intermediate 23) was reacted with 2-methoxy-5-methylphenylsulfonyl chloride according to the procedure of Intermediate 19. Yield: 0.05 g (33%) after preparative HPLC (System F; 10-50% MeCN). HPLC purity 93%, RT=1.87 min (System A; 10-97% MeCN over 3 min). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08 (t, J=7.0 Hz, 3H) 1.16 (t, J=7.0 Hz, 3H) 2.20 (s, 3H) 3.08-3.45 (m, 7H) 3.58-3.73 (m, 4H) 3.87 (s, 3H) 4.40 (s, 2H) 6.61 (d, J=1.8 Hz, 1H) 6.85 (d, J=2.0 Hz, 1H) 6.93 (d, J=1.8 Hz, 1H) 7.04 (d, J=8.5 Hz, 1H) 7.32 (dd, J=8.8, 2.0 Hz, 1H) 7.52 (d, J=1.8 Hz, 1H) 7.89 (d, J=2.3 Hz, 1H) 9.75 (s, 1H) 10.07 (s, 1H) MS (ESI+) m/z 515.4 (M+H)+.

Sources & evidence

ORD record
ord-65a0409735f449fc8ba3935f66ae2e79
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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