Tetrahydropyran-4-ylacetic acid → HCID 72191468, compound

HRID 873562Notes

Reaction equation

HRID 873562 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15]C(C)(C)C)=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[O:22]1[CH2:27][CH2:26][CH:25]([CH2:28]C(O)=O)[CH2:24][CH2:23]1.C(O[C:40]([N:42]1[CH2:45][CH:44]([C:46]([OH:48])=O)[CH2:43]1)=O)C1C=CC=CC=1>>[N:10]1[CH:9]=[CH:8][CH:7]=[C:40]([N:42]2[CH2:43][CH:44]([C:46]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([O:6][CH:7]4[CH2:8][CH2:9][N:10]([C:13](=[O:15])[CH2:28][CH:25]5[CH2:24][CH2:23][O:22][CH2:27][CH2:26]5)[CH2:11][CH2:12]4)=[CH:20][CH:21]=3)=[O:48])[CH2:45]2)[CH:11]=1

Participants

4

Reactant 3

HCID 2773575Tetrahydropyran-4-ylacetic acidHCID 109882141-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acidHCID 22181157tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate

Product 1

HCID 72191468HCID 72191468, compound

Procedure

The title compound was prepared as described in Example 1A, substituting N-(4-(piperidin-4-yloxy)phenyl)-1-(pyridin-3-yl)azetidine-3-carboxamide for tert-butyl 4-(4-aminophenoxy)piperidine-1-carboxylate and 2-(tetrahydro-2H-pyran-4-yl)acetic acid for 1-(benzyloxycarbonyl)azetidine-3-carboxylic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.95 (bs, 1H), 7.93 (d, J=4.2 Hz, 1H), 7.88-7.83 (m, 1H), 7.55-7.47 (m, 2H), 7.26-7.08 (m, 1H), 7.01-6.78 (m, 3H), 4.14-4.04 (m, 2H), 4.02-3.62 (m, 6H), 2.37-1.73 (m, 6H), 1.66-1.00 (m, 8H); MS (ESI(+)) m/e 479 (M+H)+.

Sources & evidence

ORD record
ord-2ea5baaee648483283d6a6af4351f43e
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

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