Sodium Hydroxide → HCID 90410378, compound

HRID 1403732Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[S:22](=[O:24])(=[O:23])[N:21](C(OC)=O)[CH2:20][CH2:19][CH:18]3[CH3:29])=[C:12]([F:30])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[OH-].[Na+]>CO.O>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[CH:18]([CH3:29])[CH2:19][CH2:20][NH:21][S:22]3(=[O:24])=[O:23])=[C:12]([F:30])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of methyl 6-{[4-(4-acetylpiperazin-1-yl)-2-fluorophenyl]methyl}-5-methyl-1,1- dioxo-1λ6,2,6-thiadiazinane-2-carboxylate (420 mg, 0.95 mmol) and NaOH (76 mg, 1.90 mmol) in MeOH/H2O (1:1, 10 mL) was stirred at 0° C. for 10 minutes and ambient temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. The crude product was purified by reverse phase column chromatography (1% (NH4)2CO3) to afford 2-{[4-(4-acetylpiperazin-1-yl)-2-fluorophenyl]methyl}-3-methyl-1λ6,2,6-thiadiazinane-1,1-dione as white solid (300 mg, 82%). 1H NMR (500 MHz, CDCl3) δ 7.42 (t, 1H), 6.68 (dd, 1H), 6.54 (dd, 1H), 4.373 (d, 1H), 4.22 (d, 1H), 3.85-3.90 (m, 1H), 3.76 (t, 2H), 3.61 (t, 2H), 3.53 (dd, 2H), 3.14-3.20 (m, 4H), 2.14 (s, 3H), 1.58-1.67 (m, 2H), 1.23 (d, 3H).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customThe crude product was purified by reverse phase column chromatography (1% (NH4)2CO3)

Sources & evidence

ORD record: ord-2c5ea5c5e34a409fab9250ed6ab714ec
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912219B2

Reaction notes

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