Water → 6-[2-Amino-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-4-[2-(2-methoxy-ethoxy)-ethoxy]-quinoline-3-carbonitrile

HRID 1297652Notes

Reaction equation

[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13]#[N:14])=[C:6]2[O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])=O.COC1C=CC(/C=[C:38]2/[C:39]([NH:41][C:42]([S:44]/2)=[NH:43])=[O:40])=CC=1OC1CCCC1.C([O-])(=O)C.[Na+].O>C(O)(=O)C>[NH2:43][C:42]1[S:44]/[C:38](=[CH:1]\[C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[N:9]=[CH:8][C:7]([C:13]#[N:14])=[C:6]3[O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])/[C:39](=[O:40])[N:41]=1

Participants

Conditions

Temperature: 130 °C

Procedure

The suspension of 6-formyl-4-[2-(2-methoxy-ethoxy)-ethoxy]-quinoline-3-carbonitrile (example 28b, 50 mg, 0.17 mmol), pseudothiohydantoin (19.3 mg, 0.17 mmol), and sodium acetate (55 mg, 0.68 mmol) in acetic acid (180 uL) was stirred at 130° C. for 12 h. After cooling to room temperature, water was added. The solid was collected by filtration, washed with water and dried. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-7% methanol in methylene chloride in 30 min) afforded 6-[2-amino-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-4-[2-(2-methoxy-ethoxy)-ethoxy]-quinoline-3-carbonitrile (16.2 mg, 24%) as a slight yellow solid. LC-MS m/e 399 (MH+).

Workup

temperatureAfter cooling to room temperature
filtrationThe solid was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-16ef4741adfc4460af9252b39af966ff
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250515B2

Reaction notes

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