Triethylamine → 1,1-dimethylethyl 4-[4-[(methyl[(1R)-1,2,3,4-tetrahydro-1-naphthalenyl]amino]carbonyl]-2-thiazolyl]-1-piperidinecarboxylate

HRID 2043723

반응식

HRID 2043723 반응식
[C:1]([C:4]1[N:5]=[C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[S:7][CH:8]=1)([OH:3])=O.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[CH3:41][NH:42][C@H:43]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH2:46][CH2:45][CH2:44]1>ClCCl>[CH3:41][N:42]([C@H:43]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH2:46][CH2:45][CH2:44]1)[C:1]([C:4]1[N:5]=[C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[S:7][CH:8]=1)=[O:3]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27955312-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)-1,3-thiazole-4-carboxylic acid2회HCID 7128544(R)-N-Methyl-1,2,3,4-tetrahydronaphthalen-1-amine2회

생성물 1

HCID 674599981,1-dimethylethyl 4-[4-[(methyl[(1R)-1,2,3,4-tetrahydro-1-naphthalenyl]amino]carbonyl]-2-thiazolyl]-1-piperidinecarboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A mixture of 1-(1,1-dimethylethyl) 4-[4-carboxy-2-thiazolyl]-1-piperidinecarboxylate (i.e. the product of Example 1, Step B) (3.84 g, 12.29 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (2.36 g, 12.29 mmol) and triethylamine (2.3 mL, 16.76 mmol) in 50 mL dichloromethane was stirred for 15 minutes at room temperature. (1R)-1,2,3,4-Tetrahydro-N-methyl-1-naphthalenamine (i.e. the product of Example 6, Step A) (2.18 g, 13.5 mmol) was added and the reaction mixture was stirred for 16 h. The reaction mixture was diluted with 20 mL of dichloromethane, washed with 1 N aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate solution, water and brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography using 20% to 100% of ethyl acetate in hexanes to give 2.4 g of the title compound as an oil.

후처리

  1. stirringthe reaction mixture was stirred for 16 h
  2. washwashed with 1 N aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate solution, water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-4f01cc7ef62648f4a79851583c2999b0
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586611B2

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