Triethylamine → HCID 11950360, compound

HRID 251448

Reaction equation

HRID 251448 reaction equation
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

Participants

7

Reactant 5

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

Product 1

HCID 11950360HCID 11950360, compoundYield 113.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-624893e5f2aa4271acb0cfd5c42242e3
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Linked notes

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