Diisopropylethylamine → HCID 58995057, compound

HRID 536949Notes

Reaction equation

HRID 536949 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([C:18]3[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH:19]=3)[CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[C:26]([C:28]1[CH:29]=[C:30]([C:33](O)=[O:34])[NH:31][CH:32]=1)#[N:27].Cl.CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:1][O:2][C:3]([C:5]1([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:33]([C:30]3[NH:31][CH:32]=[C:28]([C:26]#[N:27])[CH:29]=3)=[O:34])=[C:13]([C:18]3[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH:19]=3)[CH:12]=2)[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)=[O:4]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 118048114-cyano-1H-pyrrole-2-carboxylic acidHCID 58994988HCID 58994988, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 58995057HCID 58995057, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[4-amino-3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-tetrahydro-pyran-4-carboxylic acid methyl ester (as prepared in Example 16, step (d), 68.7 mg, 0.200 mmol), 4-cyano-1H-pyrrole-2-carboxylic acid (Canadian J. Chem. 59, 2673 (1981), 40.8 mg, 0.300 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (57.5 mg, 0.300 mmol), hydroxybenzotriazole (HOBt) (40.5 mg, 0.300 mmol) and DIEA (105 μL, 0.600 mmol) in 2.5 mL of DMF was stirred at RT for 2 d under Ar. The resulting mixture was treated with H2O (20 mL) and extracted with EtOAc (2×25 mL). The combined organic layers were washed with H2O (10 mL) and brine (10 mL). After drying over Na2SO4 and concentrating in vacuo, the residue was purified by silica gel chromatography (10-20% EtOAc/DCM) to afford the title compound (46 mg, 50%) as a white solid. Mass spectrum (ESI, m/z): Calcd. for C27H31N3O4, 462.2 (M+H). found 462.2.

Workup

  1. extractionextracted with EtOAc (2×25 mL)
  2. washThe combined organic layers were washed with H2O (10 mL) and brine (10 mL)
  3. dry with materialAfter drying over Na2SO4
  4. concentrationconcentrating in vacuo
  5. customthe residue was purified by silica gel chromatography (10-20% EtOAc/DCM)

Sources & evidence

ORD record
ord-882173fc96bc4e19b02337fdc55158b1
Source dataset
uspto-grants-2014_10
Patent number
US08859602B2

Reaction notes

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