Hydrochloric Acid → HCID 178461990, compound

HRID 1983603Notes

Reaction equation

[CH3:1][C:2]1([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[S:6][C:5]([NH:7][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[CH3:9])=[N:4][C:3]1=[O:20].[OH-:29].[K+].Cl>CC(O)(C)C>[CH3:1][C:2]1([C:21]2[CH:22]=[CH:23][C:24]([C:25]([NH2:26])=[O:29])=[CH:27][CH:28]=2)[S:6][C:5]([NH:7][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:17])([F:18])[F:19])[CH3:9])=[N:4][C:3]1=[O:20]

Participants

Conditions

Temperature: 85 °C

Procedure

A stirred mixture of 4-(5-methyl-4-oxo-2-((S)-1 -(2-(trifluoromethyl)phenyl) ethylamino)-4,5-dihydrothiazol-5-yl)benzonitrile (0.080 g, 0.20 mmol), prepared according to Example 1, and potassium hydroxide (0.14 g, 2.6 mmol) and t-BuOH (2 mL) was gradually heated to 85° C. After 1 h, 2N HCl was added to the reaction mixture until the pH reached 7-8. The reaction mixture was extracted with CH2Cl2 three times (50 mL). The organic phase was dried over Na2SO4, concentrated in vacuo. The crude product was purified by preparative TLC: 10% MeOH—CH2Cl2. The product (3a) was obtained as a white solid. MS (ESI, pos. ion) m/z: 422 (M+1), 420 (M-1). 1H NMR (CDCl3, 400 MHz): δ1.73-1.77 (m, 3H), 1.98, 2.08 (s, 3H), 5.04 (q, J=8 Hz, 1H), 6.17-6.39 (m, 2H), 7.36-7.42 (m, 2H), 7.52-7.75 (m 4H), 7.80-7.86 (m, 2H).

Workup

customprepared
extractionThe reaction mixture was extracted with CH2Cl2 three times (50 mL)
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated in vacuo
customThe crude product was purified by preparative TLC

Sources & evidence

ORD record: ord-07716c2709124b52ab4fc105be4871ae
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541474B2

Reaction notes

Loading…