Hydrochloric Acid → [6-Ethynyl-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 1517091노트

반응식

HRID 1517091 반응식
[CH3:1][C:2]1[C:3]([C:24]([N:26]2[CH2:31][CH2:30][CH:29]([N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[CH2:28][CH2:27]2)=[O:25])=[N:4][C:5]([C:18]#[C:19][Si](C)(C)C)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CCO.C1COCC1>[C:18]([C:5]1[N:4]=[C:3]([C:24]([N:26]2[CH2:31][CH2:30][CH:29]([N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[CH2:28][CH2:27]2)=[O:25])[C:2]([CH3:1])=[CH:7][C:6]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:16])([F:17])[F:15])[CH:9]=1)#[CH:19]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 57441155[3-Methyl-5-(3-trifluoromethyl-phenyl)-6-trimethylsilanylethynyl-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone2회

생성물 1

HCID 57441142[6-Ethynyl-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone수율 79%

시약·촉매·용매 1

HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

A solution of 0.65 g (1.27 mmol) of [3-methyl-5-(3-trifluoromethyl-phenyl)-6-trimethylsilanylethynyl-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (intermediate 12) in 12 ml of EtOH/THF (5:1) was treated at RT with 0.35 g (2.53 mmol) of potassium carbonate. After 4 hours, the reaction mixture was poured into crashed ice, the pH was adjusted to 3-4 with hydrochloric acid (2 molar) and the mixture was extracted three times with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 9:1) to give 0.439 g (79%) of the title compound as brown solid. MS: 442.3 (MH+).

후처리

  1. additionthe reaction mixture was poured
  2. extractionthe mixture was extracted three times with CH2Cl2
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 9:1)

출처 및 근거

ORD 기록
ord-bf64054380584fe2bbf89fa59e2eefa2
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227613B2

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