Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Lithium iodide | HCID 66321 | — |
| Reactant | HCID 86700186 | HCID 86700186 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 86700187 | HCID 86700187 | — |
Reaction Steps
To a stirred solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(2-(methylamino)quinolin-6-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate (4.1 mg, 0.006 mmol)) in pyridine (0.4 mL) was added LiI (50 mg, excess). The reaction mixture was heating in a microwave at 170° C. for 90 min. The mixture was concentrated in vacuo and then purified by reverse phase HPLC, eluting by 0-100% acetonitrile in H2O with 0.1% TFA to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C35H32ClN4O3S: 623.2; found: 623.2. 1H NMR (400 MHz, CD3OD) δ 8.82 (d, J=5.2 Hz, 1H), 8.60 (s, 1H), 8.57 (s, 1H), 8.53 (d, J=8.8 Hz, 1H), 8.34 (d, J=9.6 Hz, 1H), 8.22-7.20 (m, 3H), 7.70 (d, J=9.2 Hz, 1H), 7.61 (s, 3H), 7.07 (d, J=8.4 Hz, 1H), 5.28 (s, 1H), 3.24 (s, 3H), 2.64 (s, 3H), 0.98 (s, 9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08987250B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-127e21f527f245acaa1feea7a91eaf1c |
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| Source note | uspto-grants-2015_03 |
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