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Triethylamine → 6-chloro-N-[1-(hydroxymethyl)cyclohexyl]nicotinamide

HRID 251448
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HRID 251448 반응식
C(N(CC)CC)C.O.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[Cl:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([OH:38])=O)=[CH:34][N:33]=1.[NH2:41][C:42]1([CH2:48][OH:49])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>ClCCl>[Cl:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([NH:41][C:42]2([CH2:48][OH:49])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)=[O:38])=[CH:34][N:33]=1
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참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 792226-Chloronicotinic acidHCID 409153(1-Aminocyclohexyl)methanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178526939HCID 178526939, 화합물

생성물 1

HCID 119503606-chloro-N-[1-(hydroxymethyl)cyclohexyl]nicotinamide
수율 113.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Triethylamine (2.2 ml, 16.12 mmol, 2 eq), hydroxybenzotriazole hydrate (0.217 g, 1.61 mmol, 0.2 eq), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.7 g, 8.87 mmol, 1.1 eq) are added to a cold (ice bath) solution of 6-chloronicotinic acid (1.27 g, 8.06 mmol, 1 eq) and (1-aminocyclohexyl)methanol (1.04 g, 8.06 mmol, 1 eq) in dichloromethane (80 ml), stirred 30 min at 0° C. and then at room temperature for 1 h. The organic layer is then washed with water, with a saturated solution of aqueous sodium hydrogenocarbonate and dried over magnesium sulfate. The solvent is finally removed to give 2.46 g of a yellow oil.

후처리

  1. waitat room temperature for 1 h
  2. washThe organic layer is then washed with water, with a saturated solution of aqueous sodium hydrogenocarbonate
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent is finally removed

출처 및 근거

ORD 기록
ord-624893e5f2aa4271acb0cfd5c42242e3
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07863450B2

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