o-Toluenesulfonyl chloride → 2-Methyl-N-{7-[(2-methylpiperazin-1-yl)methyl]-1-benzofuran-5-yl}benzenesulfonamide dihydrochloride

HRID 1162055Notes

Reaction equation

HRID 1162055 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:11][N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH:13]2[CH3:25])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[C:26]1([CH3:36])[C:27]([S:32]([Cl:35])(=[O:34])=[O:33])=[CH:28][CH:29]=[CH:30][CH:31]=1>>[ClH:35].[ClH:35].[CH3:36][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32]([NH:1][C:2]1[CH:3]=[C:4]([CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH:13]2[CH3:25])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1)(=[O:34])=[O:33]

Participants

3

Reactant 2

HCID 8623o-Toluenesulfonyl chlorideHCID 66892829Tert-butyl 4-[(5-amino-1-benzofuran-7-yl)methyl]-3-methylpiperazine-1-carboxylate

Product 1

HCID 668935462-Methyl-N-{7-[(2-methylpiperazin-1-yl)methyl]-1-benzofuran-5-yl}benzenesulfonamide dihydrochlorideYield 48%

Procedure

The title product was prepared according to the procedure of Example 112, Step 3, starting from tert-butyl 4-[(5-amino-1-benzofuran-7-yl)methyl]-3-methylpiperazine-1-carboxylate (45 mg crude material, 0.10 mmol; obtained in Example 112, Step 2) and o-toluenesulfonyl chloride (22 μL, 0.15 mmol). The title compound (17 mg, 35%) was obtained as an off-white solid. HPLC 99%, RT=1.42 min (System A; 10-97% MeCN over 3 min), 100%, RT=1.26 min (System B; 10-97% MeCN over 3 min). 1H NMR (400 MHz, methanol-d4) δ ppm 1.69-1.74 (m, 3H) 2.67 (s, 3H) 3.37-3.62 (m, 5H) 3.67-3.75 (m, 1H) 3.84-3.95 (m, 1H) 4.57-4.65 (m, 1H) 4.90-4.97 (m, J=13.55 Hz, 1H) 6.86 (d, J=2.26 Hz, 1H) 7.23-7.29 (m, J=7.65, 7.65 Hz, 1H) 7.31 (d, J=2.01 Hz, 1H) 7.32-7.36 (m, 1H) 7.40-7.46 (m, 1H) 7.50 (d, J=2.01 Hz, 1H) 7.85-7.90 (m, 2H). MS (ESI+) for C21H25N3O3S m/z 400 (M+H)+.

Workup

  1. customThe title product was prepared

Sources & evidence

ORD record
ord-878adc37adb84c1ebbf66fcf10dbaf89
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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