4-(3-Carboxy-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester → 3-[3-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzamido]4-methyl-N-(3-morpholinophenyl)benzamide
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18](O)=[O:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].NCC1[CH:27]=[C:28]([CH:44]=[CH:45]C=1)[C:29]([NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)[CH:33]=1)=[O:30]>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18]([NH:8][C:9]2[CH:27]=[C:28]([CH:44]=[CH:45][C:10]=2[CH3:11])[C:29]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([N:38]3[CH2:39][CH2:40][O:41][CH2:42][CH2:43]3)[CH:33]=2)=[O:30])=[O:19])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
3
Procedure
Using an analogous procedure to that described in Example 18, 3-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoic acid was reacted with 3-aminomethyl-N-(3-morpholinophenyl)benzamide to give 3-[3-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzamido]4-methyl-N-(3-morpholinophenyl)benzamide in 42% yield; NMR Spectrum: (DMSOd6) 1.38 (s, 9H), 1.54 (m, 2H), 1.91 (m, 2H), 2.27 (s, 3H), 3.06 (t, 4H), 3.2 (m, 2H), 3.64 (m, 2H), 3.72 (t, 4H), 5.01 (m, 1H), 6.66 (m, 1H), 7.18 (m, 2H), 7.28 (d, 1H), 7.4 (m, 3H), 7.56 (m, 2H), 7.77 (m, 1H), 7.92 (s, 1H), 9.98 (s, 1H), 10.01 (s, 1H).
Sources & evidence
- ORD record
- ord-4f785961818c45db814414e927672903
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06821965B1
Reaction notes
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