Lithium iodide → HCID 86700263, compound

HRID 879455Notes

Reaction equation

HRID 879455 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:34]([CH3:35])=[CH:33][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[C:26]([O:31]C)=[N:27][CH:28]=[CH:29][CH:30]=4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[I-].[Li+]>N1C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C@@H:6]([C:12]1[C:34]([CH3:35])=[CH:33][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[C:26](=[O:31])[NH:27][CH:28]=[CH:29][CH:30]=4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 66321Lithium iodideHCID 86700264HCID 86700264, compound

Product 1

HCID 86700263HCID 86700263, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2′-methoxy-2,3′-bipyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (24.2 mg, 0.040 mmol) and lithium iodide (150 mg) in pyridine (2.0 mL) was heated in microwave at 170° C. for 3.5 hours. Reaction mixture was cooled to room temperature and allowed to stand for 14 days, diluted with ethyl acetate. Organic layer was washed with 5% AcOH solution (3×), brine, dried (MgSO4), filtered, concentrated, and purified using Gilson HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA) to give desired product. LCMS-ESI+: calc'd for C30H27ClN3O4S: 560.1 (M+H+); Found: 560.2 (M+H+). 1H NMR (400 MHz, CD3OD) δ 8.99 (s, 1H), 8.78 (dd, J=11.1, 6.9 Hz, 2H), 8.28 (d, J=6.0 Hz, 1H), 7.94 (s, 1H), 7.85 (d, J=6.1 Hz, 1H), 7.69 (d, J=8.6 Hz, 1H), 7.64-7.53 (m, 3H), 6.73 (dd, J=6.8 Hz, 1H), 5.28 (s, 1H), 2.62 (s, 3H), 0.97 (s, 9H).

Workup

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. washOrganic layer was washed with 5% AcOH solution (3×), brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-a5afe005f5f44d199f0205d4780e87f4
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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