Diisopropylethylamine → HCID 67513884, compound

HRID 2278415Notes

Reaction equation

HRID 2278415 reaction equation
[CH3:1][CH:2]1[O:7][CH:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.C(N(C(C)C)CC)(C)C.[ClH:18].[N:19]1(C(=N)N)[CH:23]=[N:22]C=N1>CN(C)C=O.CCOCC>[ClH:18].[CH3:8][CH:6]1[O:7][CH:2]([CH3:1])[CH2:3][N:4]([C:23](=[NH:19])[NH2:22])[CH2:5]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1108622,6-DimethylmorpholineHCID 162185151H-1,2,4-Triazole-1-carboximidamide--hydrogen chloride (1/1)

Product 1

HCID 67513884HCID 67513884, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,6-dimethylmorpholine (6.16 ml, 50.0 mmol) (Fluka, a 2.5:1 mixture of cis:trans isomers), diisopropylethylamine (8.73 ml, 50.0 mmol) and 1H-1,2,4-triazole-1-carboximidamide hydrochloride (6.11 g, 55 mmol) in N,N-dimethylformamide (20 ml) was stirred at room temperature for 24 hours. The suspension was diluted with ether (50 ml) and the reaction mixture was stirred at room temperature for 10 minutes. The ether layer was decanted off. Ether (50 ml) was added and the process repeated twice. The solid was collected, washed with ether and dried to give the title compound as a colourless solid (7.1 g, 73%) as a 2.3:1 mixture of cis:trans isomers. LC/MS [M+H]+=158.

Workup

  1. additiona 2.5:1 mixture of cis
  2. customThe ether layer was decanted off
  3. additionEther (50 ml) was added
  4. customThe solid was collected
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-384453af0e284ebc8895553c5010337c
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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