1-(4-Amino-phenyl)-piperidin-4-one hydrochloride → 5-(5-Trifluoromethyl-pyridin-2-sulfonyl)-thiophene-2-sulfonic acid [4-(4-oxo-piperidin-1-yl)-phenyl]-amide

HRID 1794850Notes

Reaction equation

HRID 1794850 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[CH:5][C:6]([S:9]([C:12]2[S:16][C:15]([S:17](Cl)(=[O:19])=[O:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[N:7][CH:8]=1.Cl.[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:36][CH2:35][C:34](=[O:37])[CH2:33][CH2:32]2)=[CH:27][CH:26]=1>>[O:37]=[C:34]1[CH2:35][CH2:36][N:31]([C:28]2[CH:29]=[CH:30][C:25]([NH:24][S:17]([C:15]3[S:16][C:12]([S:9]([C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:22])([F:21])[F:1])=[CH:8][N:7]=4)(=[O:11])=[O:10])=[CH:13][CH:14]=3)(=[O:19])=[O:18])=[CH:26][CH:27]=2)[CH2:32][CH2:33]1

Participants

3

Reactant 2

HCID 222202401-(4-Amino-phenyl)-piperidin-4-one hydrochlorideHCID 222204075-(5-Trifluoromethyl-pyridine-2-sulfonyl) thiophene-2-sulfonyl chloride

Product 1

HCID 865845715-(5-Trifluoromethyl-pyridin-2-sulfonyl)-thiophene-2-sulfonic acid [4-(4-oxo-piperidin-1-yl)-phenyl]-amide

Procedure

The title compound was prepared from 5-(5-trifluoromethyl-pyridin-2-sulfonyl)-thiophene-2-sulphonyl chloride and 1-(4-amino-phenyl)-piperidin-4-one (which was obtained in Example 224) according to the procedure B of Example 225 as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 2.37 (t, J=4.5 Hz, 4 H), 3.52 (t, J=4.5 Hz, 4 H), 6.90–7.10 (m, 4 H), 7.90 (d, J=1.2 Hz, 1 H), 8.41 (d, J=6.3 Hz, 1 H), 8.50 (d, J=1.2 Hz, 1 H), 8.62 (dd, J=6.3, 1.5 Hz, 1 H), 9.23 (s, 1 H), 9.89 (s, 1 H); MS (ES) m/z: 545.9 (MH+); HRMS Calcd. for C21H19F3N3O5S3 (MH+): 546.0439. Found: 546.0466. Anal. Calcd. for C21H18F3N3O5S3: C, 46.23; H, 3.33; N, 7.70. Found: C, 46.46; H, 3.39; N, 7.35.

Sources & evidence

ORD record
ord-22009e489e364a84aad1fbd0d025e8a7
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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