Diisopropylethylamine → HCID 67990064, compound

HRID 1184399Notes

Reaction equation

HRID 1184399 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:20](O)=[O:21])[N:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:4][CH:3]=1.ClC(N(C)C)=C(C)C.[NH2:31][C@@H:32]1[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]1[OH:38].C(N(CC)C(C)C)(C)C>ClCCl.CN(C)C=O>[OH:38][C@@H:33]1[CH2:34][CH2:35][CH2:36][CH2:37][C@H:32]1[NH:31][C:20]([C:10]1[N:11]=[N:12][C:13]([O:14][CH2:15][C:16]([F:18])([F:19])[F:17])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:9]=1)=[O:21]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 735777(1R,2R)-2-AminocyclohexanolHCID 66678582HCID 66678582, compound

Product 1

HCID 67990064HCID 67990064, compoundYield 83,587.297%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 0.300 mg 5-(4-chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-pyridazine-3-carboxylic acid in 1 ml dichloromethane was added 0.137 mL 1-chloro-N,N,2-trimethyl-propenylamine and the mixture was stirred at ambient temperature for 30 min. The resulting slightly yellow solution was added to a solution of 130 mg (1R,2R)-2-amino-cyclohexanol and 0.224 ml N,N-diisopropylethylamine in 3 ml dimethylformamide and the mixture was stirred at ambient temperature for 3 h. The reaction mixture was partitioned between 10% aqueous citric acid and ethyl acetate. The phases were separated and the organic phase was purified by chromatography on silica gel using a gradient of heptane:ethyl acetate of 95:5 to 50:50 to yield 324 mg of the title compound as white solid. MS (EI): 430.3 (M+H).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 3 h
  2. customThe reaction mixture was partitioned between 10% aqueous citric acid and ethyl acetate
  3. customThe phases were separated
  4. customthe organic phase was purified by chromatography on silica gel using a gradient of heptane

Sources & evidence

ORD record
ord-8c6f7d7fb62e4633aedfd432011d16ab
Source dataset
uspto-grants-2014_03
Patent number
US08669254B2

Reaction notes

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