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

HRID 1642442노트

반응식

HRID 1642442 반응식
[CH3:1][C:2]1[N:3]=[C:4]2[S:22][CH:21]=[CH:20][N:5]2[C:6](=[O:19])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1.[CH:23]1([CH2:26][O:27][C:28]2[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:29]=2[CH:30]=O)[CH2:25][CH2:24]1.[O-]CC.[Na+]>C(O)C>[CH:23]1([CH2:26][O:27][C:28]2[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:29]=2/[CH:30]=[CH:1]/[C:2]2[N:3]=[C:4]3[S:22][CH:21]=[CH:20][N:5]3[C:6](=[O:19])[C:7]=2[C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:17])([F:18])[F:16])=[CH:10][CH:9]=2)[CH2:24][CH2:25]1

참가 물질

5

반응물 3

HCID 2723922Sodium ethoxideHCID 66753265HCID 66753265, 화합물HCID 86636080HCID 86636080, 화합물

생성물 1

HCID 444674647-[(E)-2-(2-Cyclopropylmethoxy-3-fluorophenyl)-1-ethenyl]-6-[4-(trifluoro methoxy)-phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one수율 44.8%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

The title compound was synthesized by condensation of Intermediate 15 (350 mg, 1.071 mmol) with 2-cyclopropylmethoxy-3-fluorobenzaldehyde (291 mg, 1.501 mmol) in presence of sodium ethoxide (146 mg, 2.147 mmol) in ethanol (15 ml) according to the procedure outlined in Example 24 to give 241 mg of the desired product as a light yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 0.23 (d, J=4.8 Hz, 2H), 0.48 (d, J=6.6 Hz, 2H), 0.95-1.05 (m, 1H), 3.77 (d, J=6.9 Hz, 2H), 7.00-7.09 (m, 2H), 7.15-7.23 (m, 2H), 7.42-7.50 (m, 4H), 7.53 (d, J=4.8 Hz, 1H), 7.98-8.08 (m, 2H); ESI-MS (m/z) 503.55 (M+H)+.

출처 및 근거

ORD 기록
ord-6684b4e108ed4fcdade3792e59d7c7b7
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119647B2

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