tert-Butyl 4-(3-chloropropyl)piperazine-1-carboxylate → Tert-butyl 4-[3-[[4-(4-amino-2-fluoro-phenoxy)-6-methoxy-7-quinolyl]oxy]propyl]piperazine-1-carboxylate
Reaction equation
[F:1][C:2]1[CH:21]=[C:20]([N+:22]([O-])=O)[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([OH:17])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1.Cl[CH2:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]1>>[NH2:22][C:20]1[CH:19]=[CH:18][C:3]([O:4][C:5]2[C:14]3[C:9](=[CH:10][C:11]([O:17][CH2:26][CH2:27][CH2:28][N:29]4[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:39])([CH3:41])[CH3:40])=[O:36])[CH2:31][CH2:30]4)=[C:12]([O:15][CH3:16])[CH:13]=3)[N:8]=[CH:7][CH:6]=2)=[C:2]([F:1])[CH:21]=1Participants
3
Procedure
T1 was prepared from 4-(2-fluoro-4-nitro-phenoxy)-6-methoxy-quinolin-7-ol and tert-butyl 4-(3-chloropropyl)piperazine-1-carboxylate following the general procedure reported in Preparative Example 54 Step 1-2. 1H NMR (400 MHz, d6-DMSO, 300K) δ 1.38 (s, 9H), 1.96 (m, 2H), 2.23 (m, 4H), 2.47 (m, 2H), 3.30 (m, 4H), 3.92 (s, 3H), 4.17 (t, J=6.3 Hz, 2H), 5.46 (br s, 2H), 6.37 (d, J=5.2 Hz, 1H), 6.45 (dd, J=8.9 Hz, J=1.8 Hz, 1H), 6.54 (dd, J=13.1 Hz, J=2.4 Hz, 1H), 7.05 (t, J=8.9 Hz, 1H), 7.35 (s, 1H), 7.49 (s, 1H), 8.42 (d, J=5.2 Hz, 1H). MS (ES) C29H35FN4O5 requires: 526. Found: 527 (M+H)+.
Sources & evidence
- ORD record
- ord-d4cf82c51fdf49e7b841903c5c0ef683
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999982B2
Reaction notes
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