Sodium ethoxide → 7-[(E)-2-(2-Cyclobutylmethoxy-3-methoxyphenyl)-1-ethenyl]-6-[4-(trifluoro methyl)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1642430노트

반응식

HRID 1642430 반응식
[CH3:1][C:2]1[N:3]=[C:4]2[S:21][CH:20]=[CH:19][N:5]2[C:6](=[O:18])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.[CH:22]1([CH2:26][O:27][C:28]2[C:35]([O:36][CH3:37])=[CH:34][CH:33]=[CH:32][C:29]=2[CH:30]=O)[CH2:25][CH2:24][CH2:23]1.[O-]CC.[Na+]>C(O)C>[CH:22]1([CH2:26][O:27][C:28]2[C:35]([O:36][CH3:37])=[CH:34][CH:33]=[CH:32][C:29]=2/[CH:30]=[CH:1]/[C:2]2[N:3]=[C:4]3[S:21][CH:20]=[CH:19][N:5]3[C:6](=[O:18])[C:7]=2[C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:10][CH:9]=2)[CH2:23][CH2:24][CH2:25]1

참가 물질

5

반응물 3

HCID 2723922Sodium ethoxideHCID 65459423HCID 65459423, 화합물HCID 667528027-Methyl-6-[4-(trifluoromethyl)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

생성물 1

HCID 444673107-[(E)-2-(2-Cyclobutylmethoxy-3-methoxyphenyl)-1-ethenyl]-6-[4-(trifluoro methyl)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one수율 46.9%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

The title compound was synthesized by condensation of Intermediate 5 (400 mg, 1.289 mmol) with 2-cyclobutylmethoxy-3-methoxybenzaldehyde (368 mg, 1.603 mmol) in the presence of sodium ethoxide (163 mg, 2.411 mmol) in ethanol (15 ml) according to the procedure described in Example 24 to give 310 mg of the desired product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.80-1.86 (m, 5H), 1.98-2.04 (m, 2H), 3.77 (s, 3H), 3.82 (d, J=6.9 Hz, 2H), 6.87-7.00 (m, 4H), 7.51 (d, J=7.5 Hz, 1H), 7.59 (d, J=7.8 Hz, 2H), 7.84 (d, J=7.8 Hz, 2H), 8.01 (d, J=4.8 Hz, 1H) 8.14 (d, J=15.6 Hz, 1H); ESI-MS (m/z) 513.30 (M+H)+.

출처 및 근거

ORD 기록
ord-05e3b01b76ce4af58ccbe1cb6409d733
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119647B2

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