Piperidine → HCID 131729824, 화합물

HRID 572305노트

반응식

HRID 572305 반응식
[F:1][C:2]([F:18])([F:17])[C:3]1[O:7][N:6]=[C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=2)[C:4]=1[CH3:16].[ClH:19].Cl.[NH:21]1[CH2:26][CH2:25][CH2:24][CH:23]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH2:22]1.N1CCCCC1>C(N(CC)CC)C.C1COCC1>[ClH:19].[CH3:16][C:4]1[C:5]([C:8]2[S:12][C:11]([C:13]([N:21]3[CH2:26][CH2:25][CH2:24][CH:23]([N:27]4[CH2:28][CH2:29][O:30][CH2:31][CH2:32]4)[CH2:22]3)=[O:15])=[CH:10][CH:9]=2)=[N:6][O:7][C:3]=1[C:2]([F:1])([F:18])[F:17]

참가 물질

6

반응물 3

HCID 8082PiperidineHCID 252109975-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acidHCID 534098974-(Piperidin-3-yl)morpholine--hydrogen chloride (1/2)

생성물 1

HCID 131729824HCID 131729824, 화합물수율 65%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매2회

실험 절차

Prepared from 5-(5-Trifluoromethyl-4-methyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and 4-piperidin-3-yl-morpholine, di-hydrochloride by the method described in Example 2 Method B reversing the order of addition such that solid acid chloride was added to a THF solution of triethylamine and piperidine derivative. An additional 2 equivalents of triethylamine was used. The reaction mixture was evaporated to an oil, triturated and filtered with the aid of water, then with a saturated aqueous NaHCO3 solution. The residual oil was then dissolved in EtOAc (2 mL), dried over MgSO4, filtered, and evaporated to an oil. The crude oil was then dissolved in diethyl ether (1 mL) and treated with a 4 N solution of hydrogen chloride in 1,4,-dioxane to precipitate product as a colorless solid. The solid was filtered with the aid of diethyl ether and air dried to afford product as a colorless solid (61 mg, 65%). LC/MS 4.66 min, [M+1]+ 430.

후처리

  1. customThe reaction mixture was evaporated to an oil
  2. customtriturated
  3. filtrationfiltered with the aid of water
  4. dissolutionThe residual oil was then dissolved in EtOAc (2 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to an oil
  8. dissolutionThe crude oil was then dissolved in diethyl ether (1 mL)
  9. additiontreated with a 4 N solution of hydrogen chloride in 1,4,-dioxane
  10. customto precipitate product as a colorless solid
  11. filtrationThe solid was filtered with the aid of diethyl ether and air
  12. customdried

출처 및 근거

ORD 기록
ord-7411c3340845499bb653cc5298a0b80c
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029397B2

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