(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5-(2-(but-3-en-1-yloxy)benzyl)-1,3,4-oxadiazol-2-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate → (2S)-2-(tert-Butoxy)-2-{4,28-dimethyl-21,27,33-trioxa-1,7,11,12,34-pentaazahexacyclo[26.2.2.16,9.110,13.02,7.015,20]tetratriaconta-2,4,6(34),8,10,12,15(20),16,18-nonaen-3-yl}acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5-(2-(but-3-en-1-yloxy)benzyl)-1,3,4-oxadiazol-2-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate | HCID 118308913 | — |
| Reactant | Methyl(2S)-2-(tert-butoxy)-2-{15-fluoro-4,26-dimethyl-10-oxo-19,25-dioxa-1,7,11,31-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl}acetate | HCID 118316265 | — |
| Reactant | (2S)-2-(tert-Butoxy)-2-{15-fluoro-4,26-dimethyl-10-oxo-19,25-dioxa-1,7,11,31-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl}acetic acid | HCID 118316266 | — |
| Product | (2S)-2-(tert-Butoxy)-2-{4,28-dimethyl-21,27,33-trioxa-1,7,11,12,34-pentaazahexacyclo[26.2.2.16,9.110,13.02,7.015,20]tetratriaconta-2,4,6(34),8,10,12,15(20),16,18-nonaen-3-yl}acetic acid | HCID 118316267 | 6% |
Reaction Steps
Prepared from (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5-(2-(but-3-en-1-yloxy)benzyl)-1,3,4-oxadiazol-2-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate in 6% yield following the procedures used to prepare methyl(2S)-2-(tert-butoxy)-2-{15-fluoro-4,26-dimethyl-10-oxo-19,25-dioxa-1,7,11,31-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl}acetate and (2S)-2-(tert-butoxy)-2-{15-fluoro-4,26-dimethyl-10-oxo-19,25-dioxa-1,7,11,31-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl}acetic acid. 1H NMR (500 MHz, DMSO-d6) δ 8.08-8.03 (m, 1H), 7.36-7.32 (m, 2H), 7.28-7.23 (m, 1H), 7.09-7.01 (m, 1H), 6.97-6.89 (m, 1H), 5.92-5.76 (m, 1H), 4.33-4.21 (m, 2H), 4.13-4.03 (m, 2H), 3.77-3.69 (m, 2H), 3.14-3.03 (m, 2H), 2.91-2.81 (m, 1H), 2.74-2.62 (m, 1H), 2.44-2.39 (m, 3H), 1.93-1.60 (m, 10H), 1.23-1.20 (m, 3H), 1.17 (s, 9H); LCMS (ESI, M+1): 618.5.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409922B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-21795edc9d7349a1a7f4c5083d74acb3 |
| Source note | uspto-grants-2016_08 |