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

HRID 2043723

反応式

HRID 2043723 の反応式
[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]

参加物

6

反応物 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 acid2 回HCID 7128544(R)-N-Methyl-1,2,3,4-tetrahydronaphthalen-1-amine2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4f01cc7ef62648f4a79851583c2999b0
出典データセット
uspto-grants-2013_11
特許番号
US08586611B2

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