Piperazine → HCID 86700430, compound

HRID 879620Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:11]1[C:26]([CH3:27])=[CH:25][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=3)[S:17][C:13]=2[C:12]=1[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].O1CCOCC1.[NH:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1.[OH-].[Na+]>C(O)C.CCN(CC)CC.O>[C:1]([O:5][C@@H:6]([C:11]1[C:26]([CH3:27])=[CH:25][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:41]4[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]4)[N:19]=3)[S:17][C:13]=2[C:12]=1[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:7]([OH:9])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A vial was charged with a solution of (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (10 mg), dioxane (500 μL), H2O (200 μL), Et3N (50 μL), and piperazine (40 mg). The reaction was heated to 60° C. for 1 h. Ethanol (absolute, 500 μL) and 5 M aq NaOH (500 μL) were added. The reaction was heated to 60° C. for 30 min. The reaction was cooled to 23° C. and directly purified by reverse phase HPLC (5-100% ACN/H2O+0.1% TFA) giving the title compound. 1H NMR (400 MHz, CD3OD) δ 8.49 (d, J=5.0 Hz, 1H), 8.03 (d, J=8.4 Hz, 1H), 7.81 (s, 1H), 7.68-7.44 (m, 3H), 7.41 (d, J=5.0 Hz, 1H), 5.08 (s, 1H), 3.92-3.69 (m, 4H), 2.85 (dd, J=18.8, 13.9 Hz, 4H), 2.66 (s, 3H), 0.91 (s, 9H). LCMS-ESI+: calc'd for C20H31ClN5O3S [M+H+]: 552.2, 554.2; Found: 552.4, 552.2 (M+H+).

Workup

temperatureThe reaction was heated to 60° C. for 30 min
temperatureThe reaction was cooled to 23° C.
customdirectly purified by reverse phase HPLC (5-100% ACN/H2O+0.1% TFA)

Sources & evidence

ORD record: ord-954aab4e6178496d950a1dd55d278159
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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