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Triethylamine → HCID 66796035, 화합물

HRID 2043788
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HRID 2043788 반응식
[CH3:1][C:2]1[N:6]([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[N:20]=[C:19]([C:21]([OH:23])=O)[CH:18]=[N:17]3)[CH2:12][CH2:11]2)=[O:9])[N:5]=[C:4]([C:24]([F:27])([F:26])[F:25])[CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:34][NH:35][C@H:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39][CH2:38][CH2:37]1.C(N(CC)CC)C>ClCCl.CN(C)C=O>[CH3:34][N:35]([C@H:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39][CH2:38][CH2:37]1)[C:21]([C:19]1[CH:18]=[N:17][N:16]([CH:13]2[CH2:12][CH2:11][N:10]([C:8](=[O:9])[CH2:7][N:6]3[C:2]([CH3:1])=[CH:3][C:4]([C:24]([F:26])([F:25])[F:27])=[N:5]3)[CH2:15][CH2:14]2)[N:20]=1)=[O:23]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 7128544(R)-N-Methyl-1,2,3,4-tetrahydronaphthalen-1-amineHCID 67463041HCID 67463041, 화합물2회

생성물 1

HCID 66796035HCID 66796035, 화합물수율 77.6%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
촉매
HCID 6344Dichloromethane용매2회

실험 절차

To a slurry of 2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-2H-1,2,3-triazole-4-carboxylic acid (0.070 g, 0.18 mmol) (i.e. the product of Example 32, Step C) in dichloromethane (2 mL) was added oxalyl chloride (0.05 mL, 0.35 mmol) and one drop of N,N-dimethylformamide. After 45 minutes the reaction mixture was concentrated in vacuo and the resulting residue was dissolved in dichloromethane (10 mL). The reaction mixture was then added to a solution of (R)—N-methyl-1,2,3,4-tetrahydronaphthalen-1-ylamine (32 mg, 0.20 mmol) and triethylamine (0.033 mL, 0.24 mmol) in dichloromethane (2 mL) at 0° C. The reaction mixture was stirred at room temperature overnight. The organic layer was washed with saturated aqueous sodium bicarbonate, dried (Na2SO4) and the solvent was removed with a rotary evaporator. The residue was purified by medium pressure liquid chromatography (MPLC) using 35-60% ethyl acetate in hexanes as eluant to afford 74 mg of the title product, a compound of the present invention as an oil.

후처리

  1. concentrationAfter 45 minutes the reaction mixture was concentrated in vacuo
  2. dissolutionthe resulting residue was dissolved in dichloromethane (10 mL)
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was removed with a rotary evaporator
  6. customThe residue was purified by medium pressure liquid chromatography (MPLC)

출처 및 근거

ORD 기록
ord-933911e859034dd28edf332beab3a10a
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08586611B2

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