Ammonia → HCID 86602682, compound

HRID 2377281Notes

Reaction equation

HRID 2377281 reaction equation
[C:1]([OH:7])(=O)[CH2:2][CH2:3][C:4]#[CH:5].ON1C2C=CC=CC=2N=N1.[NH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.N>CN(C)C=O.O>[N:21]1([CH2:20][CH2:19][NH:18][C:1](=[O:7])[CH2:2][CH2:3][C:4]#[CH:5])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

9

Reactant 6

HCID 222AmmoniaHCID 8471TriethylamineHCID 224644-Pentynoic acidHCID 757711-HydroxybenzotriazoleHCID 4082852-MorpholinoethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86602682HCID 86602682, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To 4-pentynoic acid (981 mg, 10 mmol) was added anhydrous 1-hydroxybenzotriazole (8.11 g, 60 mmol), followed by addition of N,N-dimethylformamide (55 mL) and the mixture was stirred at room temperature until a yellow solution resulted. A solution of 4-(2-aminoethyl)-morpholine (1.31 g, 10.1 mmol) in N,N-dimethylformamide (10 mL) was added, followed by addition of triethylamine (8.35 mL, 60 mmol). After stirring for about 10 min, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (6.73 g, 35 mmol) was added and stirring at room temperature was continued overnight. The reaction mixture was diluted with water and was extracted successively with diethyl ether, ethyl acetate, dichloromethane and chloroform/i-propanol (9:1). The combined organic extracts were dried (Na2SO4), filtered and concentrated under vacuum. The solid residue was purified by silica gel flash chromatography using dichloromethane/methanol (9:1) as eluent to provide Example 646. MS (DCI-NH3): m/z 211 (M+H)+.

Workup

  1. customresulted
  2. stirringAfter stirring for about 10 min
  3. stirringstirring at room temperature
  4. extractionwas extracted successively with diethyl ether, ethyl acetate, dichloromethane and chloroform/i-propanol (9:1)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe solid residue was purified by silica gel flash chromatography
  9. customto provide Example 646

Sources & evidence

ORD record
ord-d64cdacf0c874c5dac1329f81aa2233c
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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