2-Chlorobenzoxazole → HCID 67851574, compound

HRID 2294062Notes

Reaction equation

Cl.[CH3:2][O:3][C:4]1[CH:33]=[CH:32][CH:31]=[CH:30][C:5]=1[CH2:6][NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][CH2:15][CH2:16][CH2:17][NH:18]C2SC=CN=2)[C@H:9]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.BrC1SC=CN=1.[Cl:40][C:41]1[O:42][C:43]2[CH:49]=[CH:48][CH:47]=[CH:46][C:44]=2[N:45]=1>>[ClH:40].[O:42]1[C:43]2[CH:49]=[CH:48][CH:47]=[CH:46][C:44]=2[N:45]=[C:41]1[NH:18][CH2:17][CH2:16][CH2:15][CH2:14][N:10]1[CH2:11][CH2:12][CH2:13][C@H:8]([NH:7][CH2:6][C:5]2[CH:30]=[CH:31][CH:32]=[CH:33][C:4]=2[O:3][CH3:2])[C@@H:9]1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

Reactant 3

HCID 119862-Chlorobenzoxazole

HCID 764302-Bromothiazole

HCID 88385136HCID 88385136, compound

Product 1

HCID 67851574HCID 67851574, compound

Procedure

The title compound was prepared in a similar manner to the compound of Example 1 by replacing (2S, 3S)-3-(2-methoxybenzyl)amino-2-phenylpiperidine with the corresponding racemate and 2-bromothiazole with 2-chlorobenzoxazole; mp 158°-160° C. (dec.) 1H NMR (CDCl3) 67 1.58 (m, 5H), 1.90 (m, 1H), 2.04 (m, 4H), 2.20 (m, 1H), 2.56 (m, 1H), 2.71 (d, 1H, J=2), 3.25 (m, 1H), 3.38 (m, 5H), 3.57 (d, 1H, J=15), 3.96 (d, 1H, J=15), 6.60 (d, 1H, J=6), 6.76 (t, 1H, J=6), 6.96 (m, 2H), 7.12 (m, 3H), 7.28 (m, 6H). HRMS calc'd for C30H36N4O2 : 484.2838. Found: 484.2844.

Sources & evidence

ORD record: ord-47252bce3bb249279ca5842a2e7b76db
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05688804

Reaction notes

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