2-Trifluoromethylbenzenesulphonyl chloride → n-{7-[(3-Methylpiperazin-1-yl)methyl]-1-benzofuran-5-yl}-2-(trifluoromethyl)benzenesulfonamide, dihydrochloride

HRID 1162059Notes

Reaction equation

HRID 1162059 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)[CH:14]([CH3:25])[CH2:13]2)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[F:26][C:27]([F:39])([F:38])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34]([Cl:37])(=[O:36])=[O:35]>>[ClH:37].[ClH:37].[CH3:25][CH:14]1[NH:15][CH2:16][CH2:17][N:12]([CH2:11][C:4]2[C:5]3[O:9][CH:8]=[CH:7][C:6]=3[CH:10]=[C:2]([NH:1][S:34]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[C:27]([F:26])([F:38])[F:39])(=[O:36])=[O:35])[CH:3]=2)[CH2:13]1

Participants

3

Reactant 2

HCID 1366162-Trifluoromethylbenzenesulphonyl chlorideHCID 66894181Tert-butyl 4-[(5-amino-1-benzofuran-7-yl)methyl]-2-methylpiperazine-1-carboxylate

Product 1

HCID 131728391n-{7-[(3-Methylpiperazin-1-yl)methyl]-1-benzofuran-5-yl}-2-(trifluoromethyl)benzenesulfonamide, dihydrochlorideYield 53.6%

Procedure

The title compound was prepared according to the procedure of Example 115, Step 4, starting from tert-butyl 4-[(5-amino-1-benzofuran-7-yl)methyl]-2-methylpiperazine-1-carboxylate (41 mg crude starting material, 0.11 mmol; obtained in Example 115, Step 3) and 2-(trifluoromethyl)benzenesulfonyl chloride (25 μL, 0.17 mmol). The title compound (24 mg, 44%) was obtained as an off-white solid. HPLC 98%, RT=1.56 min (System A; 10-97% MeCN over 3 min), 97%, RT=1.37 min (System B; 10-97% MeCN over 3 min). 1H NMR (400 MHz, methanol-d4) δ ppm 1.41 (d, J=6.53 Hz, 3H) 3.36-3.44 (m, J=13.30, 12.05 Hz, 1H) 3.47-3.78 (m, 5H) 3.81-3.94 (m, 1H) 4.74 (s, 2H) 6.88 (d, J=2.26 Hz, 1H) 7.41 (d, J=2.01 Hz, 1H) 7.53 (d, J=2.26 Hz, 1H) 7.68-7.76 (m, 2H) 7.88 (d, J=2.01 Hz, 1H) 7.90-7.95 (m, J=6.90, 2.13 Hz, 1H) 8.09-8.13 (m, 1H). MS (ESI+) for C21H22F3N3O3S m/z 454 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-8b5e8e8ffeff42b69b3c37cbd03c3dd8
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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