Lithium iodide → HCID 86700255, compound

HRID 879446Notes

Reaction equation

HRID 879446 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:37]([CH3:38])=[CH:36][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:26]=[N:27][C:28]5[N:29]([N:31]=[CH:32][C:33]=5[CH2:34][CH3:35])[CH:30]=4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=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:37]([CH3:38])=[CH:36][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:26]=[N:27][C:28]5[N:29]([N:31]=[CH:32][C:33]=5[CH2:34][CH3:35])[CH:30]=4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:39]1[CH:40]=[CH:41][C:42]([Cl:45])=[CH:43][CH:44]=1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 66321Lithium iodideHCID 86700253HCID 86700253, compound

Product 1

HCID 86700255HCID 86700255, 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-(3-ethylpyrazolo[1,5-a]pyrimidin-6-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (31 mg, 0.048 mmol) and lithium iodide (200 mg) in pyridine (0.5 mL) was heated in microwave at 170° C. for 1 h. Reaction mixture was diluted with ethyl acetate, washed with 5% acetic acid solution, brine, dried (MgSO4), filtered, concentrated and purified by CombiFlash (0 to 10% MeOH/CH2Cl2). Lyophilization gave desired product. LCMS-ESI+: calc'd for C33H31ClN5O3S: 612.2 (M+H+); Found: 612.2 (M+H+). 1H NMR (400 MHz, CD3OD) δ 9.33 (d, J=2.1 Hz, 1H), 9.02 (d, J=2.1 Hz, 1H), 8.60 (d, J=5.1 Hz, 1H), 8.56-8.49 (m, 2H), 8.29 (s, 1H), 8.02 (s, 1H), 7.85 (tt, J=7.7, 1.8 Hz, 1H), 7.77-7.61 (m, 4H), 7.61-7.49 (m, 3H), 7.43 (ddd, J=7.7, 4.4, 1.5 Hz, 2H), 5.24 (s, 1H), 2.78 (q, J=7.6 Hz, 2H), 2.56 (s, 3H), 1.30 (t, J=7.6 Hz, 3H), 0.96 (d, J=6.8 Hz, 9H).

Workup

  1. customReaction mixture
  2. washwashed with 5% acetic acid solution, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by CombiFlash (0 to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2cb13e4da5db415aa1b9edcdb5776f44
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

Loading…