Triethylamine → HCID 11455294, compound

HRID 1833271Notes

Reaction equation

HRID 1833271 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([C:15](=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1)=[N:8][CH:7]=[C:6]2[C:25](O)=[O:26].C(N(CC)CC)C.C([O:39]C(Cl)=O)C(C)C.[C:43]1([CH:49]2[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(OCC)(=O)C.CN(C)C=O>[OH:39][C:49]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:50][CH2:51][N:52]([C:25]([C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[C:9]([C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=3)=[O:24])=[N:8][CH:7]=2)=[O:26])[CH2:53][CH2:54]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 698734-PhenylpiperidineHCID 11394498HCID 11394498, compound

Product 1

HCID 11455294HCID 11455294, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6,7-dimethoxy-1-(3-methoxy-benzoyl)-isoquinoline-4-carboxylic acid (30.0 mg, 81.65 mmol) in dry, N,N-dimethylformamide (2 mL) was chilled in an ice bath under argon. With stirring, triethylamine (14.4 uL, 102 mmol) and isobutylchloroformate (13.4 uL, 102 mmol) were added. The solution was stirred for 30 min and then 4-hydroxy, 4-phenylpiperidine (28.9 mg 1.633 mM) was added. The solution was allowed to warm to room temperature with stirring for 1 hr. and then diluted with ethyl acetate (30 mL), The ethyl acetate solution was washed sequentially with saturated sodium bicarbonate solution (2×5 mL), water (5 mL), and saturated sodium chloride solution (5 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to afford 50 mg of solid. This crude material was purified by flash chromatography, eluting with 50% ethyl acetate in hexanes (containing 1% acetic acid) and then increasing gradually to 80% ethyl acetate in hexanes After tic analysis, fractions were pooled and evaporated to yield 24 mg (55.8%) of an off-white, powder as an acetate salt: APCI-MS m/e calcd for C31H30N2O6 (M+H) 527.6, found 527; H NMR (300 MHz) compatible.

Workup

  1. stirringThe solution was stirred for 30 min
  2. stirringwith stirring for 1 hr
  3. washThe ethyl acetate solution was washed sequentially with saturated sodium bicarbonate solution (2×5 mL), water (5 mL), and saturated sodium chloride solution (5 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a330e3c9b03a47eeb9bee8ef3cd0242f
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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