5-(1-hydroxy-2-aminoethyl)-1H-indole-7-carboxamide → 5-[2-({1-[4-({[4-(Acetylamino)phenyl]sulfonyl}amino)phenyl]-4-piperidinyl}amino)-1-hydroxyethyl]-1H-indole-7-carboxamide
Reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:28][CH2:29][CH:30]([C:32]1[CH:33]=[C:34]2[C:38](=[C:39]([C:41]([NH2:43])=[O:42])[CH:40]=1)[NH:37][CH:36]=[CH:35]2)[OH:31]>>[C:25]([NH:24][C:21]1[CH:22]=[CH:23][C:18]([S:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([N:5]3[CH2:6][CH2:7][CH:2]([NH:28][CH2:29][CH:30]([C:32]4[CH:33]=[C:34]5[C:38](=[C:39]([C:41]([NH2:43])=[O:42])[CH:40]=4)[NH:37][CH:36]=[CH:35]5)[OH:31])[CH2:3][CH2:4]3)=[CH:9][CH:10]=2)(=[O:16])=[O:17])=[CH:19][CH:20]=1)(=[O:27])[CH3:26]Participants
Procedure
The title compound was prepared from N-{4-[4-(4-oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamide (which was obtained in Example 216) and 5-(2-amino-1-hydroxy-ethyl)-1H-indole-7-carboxamide according to the procedure of Example 255 as a pale grey solid; 1H NMR (300 MHz, DMSO-d6) δ 1.60–1.80 (m, 2 H), 2.00–2.15 (m, 2 H), 2.06 (s, 3 H), 2.50–2.70 (m, 2 H), 3.10–3.20 (m, 3 H), 3.60–3.75 (m, 2 H), 4.95–5.05 (m, 1 H), 6.13 (brs, 1 H), 6.49 (t, J=2.7 Hz, 1 H), 6.81 (d, J=9.0 Hz, 2 H), 6.88 (d, J=9.0 Hz, 2 H), 7.35 (t, J=2.7 Hz, 1 H), 7.42 (brs, 1 H), 7.59 (d, J=9.0 Hz, 2 H), 7.69 (d, J=9.0 Hz, 2 H), 7.77 (s, 1 H), 8.11 (s, 1 H), 9.72 (s, 1 H), 10.40 (s, 1 H); MS (ES) m/z: 591.1 (MH+); HRMS Calcd. for C30H35N6O5S (MH+): 591.2390. Found: 591.2392.
Sources & evidence
- ORD record
- ord-e960637a01134c2a94a945707cad95d7
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07022716B2
Reaction notes
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