HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → (E)-(6-{2-[Methyl-(3-methyl-benzo[b]thiophen-2-ylmethyl)carbamoyl]vinyl}-2-oxo-1,4-dihydro-2H-pyrido[2,3-d]pyrimidin-3-yl)acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | (E)-(6-{2-[Methyl-(3-methyl-benzo[b]thiophen-2-ylmethyl)carbamoyl]vinyl}-2-oxo-1,4-dihydro-2H-pyrido[2,3-d]pyrimidin-3-yl)acetic acid ethyl ester | HCID 59456952 | — |
| Reactant | (E)-(6-{2-[Methyl-(1-methyl-1H-indol-2-ylmethyl)carbamoyl]vinyl}-2-oxo-1,4-dihydro-2H-pyrido[2,3-d]pyrimidin-3-yl)acetic acid ethyl ester | HCID 66967165 | — |
| Product | (E)-(6-{2-[Methyl-(3-methyl-benzo[b]thiophen-2-ylmethyl)carbamoyl]vinyl}-2-oxo-1,4-dihydro-2H-pyrido[2,3-d]pyrimidin-3-yl)acetic acid | HCID 10026781 | 89% |
Reaction Steps
According to the procedure of Example 124 (b), except substituting (E)-(6-{2-[methyl-(3-methyl-benzo[b]thiophen-2-ylmethyl)carbamoyl]vinyl}-2-oxo-1,4-dihydro-2H-pyrido[2,3-d]pyrimidin-3-yl)acetic acid ethyl ester for the (E)-(6-{2-[methyl-(1-methyl-1H-indol-2-ylmethyl)carbamoyl]vinyl}-2-oxo-1,4-dihydro-2H-pyrido[2,3-d]pyrimidin-3-yl)acetic acid ethyl ester, the title compound (720 mg, 89%) was prepared as a light yellow solid and as a mixture of amide rotomers: 1H NMR (300 MHz, DMSO-d6) δ 10.78 (br s, 1H), 10.08 (s, 1H), 8.39 (s, 1H), 8.01 (s, 1H), 7.88 (d, J=7.5 Hz, 1H), 7.74 (d, J=7.4 Hz, 1H), 7.56-7.16 (m, 4H), 5.11-4.88 (m, 2H), 4.52 (s, 2H), 4.04 (s, 2H), 3.14-2.93 (m, 3H), 2.42 (s, 3H); MS (ESI) m/e 451 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07879872B2 |
| Source dataset | uspto-grants-2011_02 |
| ORD ID | ord-3713ed0587c04fae82660fae96c1a8c6 |
| Source note | uspto-grants-2011_02 |