N-[4-(2-aminoethyl)phenyl]Benzenesulfonamide → HCID 44307379, compound

HRID 2399876Notes

Reaction equation

HRID 2399876 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][C@@H:9]2[CH2:11][O:10]2)[CH:2]=1.[NH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])=[CH:17][CH:16]=1>>[OH:10][C@H:9]([CH2:8][O:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:11][NH:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][S:22]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)(=[O:24])=[O:23])=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 15281645N-[4-(2-aminoethyl)phenyl]BenzenesulfonamideHCID 54469224HCID 54469224, compound

Product 1

HCID 44307379HCID 44307379, compound

Procedure

In a manner analogous to that of Example 7, the title compound was prepared from the epoxide from Example 162 and N-[4-(2-aminoethyl)phenyl]benzenesulfonamide (Example 6). Purification by preparative thin layer chromatography on silica gel (eluant 90:10:2 methylen chloride/methanol/30% ammonium hydroxide) gave the title compound. 1H NMR (400 MHz, CD3OD) δ8.23 (d, 1H, J=4Hz), 8.12 (dd, 1H, J=2.4Hz), 7.71(d, 2H, J=8Hz), 7.52 (m, 1H), 7.40-7.48 (m, H), 7.35 (m, 1H), 7.09 (d, 2H, J=10Hz), 7.00 (d, 2H, J=10Hz), 3.95-4.08 (m, 3H), 2.69-2.90 (m, 6H).

Workup

  1. customPurification by preparative thin layer chromatography on silica gel (eluant 90:10:2 methylen chloride/methanol/30% ammonium hydroxide)

Sources & evidence

ORD record
ord-8756bb4c8949496a8248dedb8df35f2a
Source dataset
uspto-grants-1995_09
Patent number
US05451677

Reaction notes

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