Lithium iodide → HCID 86700257, compound

HRID 879448Notes

Reaction equation

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

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(3-ethylpyrazolo[1,5-a]pyrimidin-6-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (24.9 mg, 0.044 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 30% MeOH/CH2Cl2). Lyophilization gave desired product. LCMS-ESI+: calc'd for C28H28ClN4O3S: 535.2. (M+H+); Found: 535.2 (M+H+). 1H NMR (400 MHz, CDCl3) δ 9.22 (dd, J=2.8, 1.6 Hz, 1H), 8.95 (dd, J=2.8, 1.6 Hz, 1H), 8.07 (s, 1H), 7.89 (s, 1H), 7.70 (d, J=7.8 Hz, 1H), 7.58-7.37 (m, 3H), 5.31 (s, 1H), 2.86 (q, J=7.6 Hz, 2H), 2.58 (s, 3H), 1.34 (dd, J=7.8, 7.3 Hz, 3H), 0.99 (s, 9H).

Workup

customReaction mixture
washwashed with 5% acetic acid solution, brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
custompurified by CombiFlash (0 to 30% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-01a3f4cb035a49bdb07e64bd6a1e971a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

Loading…