Tetrahydropyran-4-ylacetic acid → HCID 86702047, compound
Reaction equation
C(O[C:9]([N:11]1[CH2:14][CH:13]([C:15]([OH:17])=O)[CH2:12]1)=O)C1C=CC=CC=1.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33]C(C)(C)C)=O)[CH2:27][CH2:26]2)=[CH:21][CH:20]=1.NC1C=CC(O[CH:44]2[CH2:49][CH2:48][N:47](C(OC(C)(C)C)=O)[CH2:46][CH2:45]2)=CC=1.[CH:59]1([C:64]2C=CC=CC=2C(O)=O)[CH2:63][CH2:62][CH2:61][CH2:60]1.O1CCC(CC(O)=O)CC1>>[CH:59]1([CH2:64][C:31]([N:28]2[CH2:27][CH2:26][CH:25]([C:22]3[CH:21]=[CH:20][C:19]([NH:18][C:15]([C@H:13]4[CH2:12][CH2:9][N:11]([C:49]5[CH:48]=[N:47][CH:46]=[CH:45][CH:44]=5)[CH2:14]4)=[O:17])=[CH:24][CH:23]=3)[CH2:30][CH2:29]2)=[O:33])[CH2:63][CH2:62][CH2:61][CH2:60]1Participants
Reactant 5
Product 1
Procedure
The title compound was prepared as described in Example 1, substituting (S)-1-((benzyloxy)carbonyl)pyrrolidine-3-carboxylic acid for 1-(benzyloxycarbonyl)azetidine-3-carboxylic acid and tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate for tert-butyl 4-(4-aminophenoxy)piperidine-1-carboxylate in Example 1A, and cyclopentylbenzoic acid for 2-(tetrahydro-2H-pyran-4-yl)acetic acid in Example 1E. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.03 (s, 1H), 7.95 (d, J=2.8 Hz, 1H), 7.85 (dd, J=4.6, 1.2 Hz, 1H), 7.55 (t, J=10.1 Hz, 2H), 7.16 (dd, J=8.3, 4.3 Hz, 3H), 6.92 (ddd, J=8.4, 2.9, 1.3 Hz, 1H), 4.54 (d, J=12.7 Hz, 1H), 3.98 (d, J=13.7 Hz, 1H), 3.64-3.48 (m, 1H), 3.48-3.38 (m, 1H), 3.22-2.87 (m, 2H), 2.68 (dd, J=24.3, 12.3 Hz, 1H), 2.41-2.01 (m, 6H), 1.77 (s, 4H), 1.68-1.04 (m, 9H); MS (ESI(+)) m/e 461 (M+H)+.
Sources & evidence
- ORD record
- ord-3d6b74a5f9184f31822bac2977c3b7a3
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975398B2
Reaction notes
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