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[ CAS No. 106675-70-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 106675-70-1
Chemical Structure| 106675-70-1
Chemical Structure| 106675-70-1
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Product Details of [ 106675-70-1 ]

CAS No. :106675-70-1 MDL No. :MFCD02326951
Formula : C6H12N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :OXSWGKZLVLVHIS-UHFFFAOYSA-N
M.W : 176.17 Pubchem ID :3287678
Synonyms :

Calculated chemistry of [ 106675-70-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.32
TPSA : 59.08 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.68
Log Po/w (XLOGP3) : -0.29
Log Po/w (WLOGP) : -0.97
Log Po/w (MLOGP) : -0.58
Log Po/w (SILICOS-IT) : -1.86
Consensus Log Po/w : -0.41

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.42
Solubility : 67.0 mg/ml ; 0.381 mol/l
Class : Very soluble
Log S (Ali) : -0.49
Solubility : 56.9 mg/ml ; 0.323 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.52
Solubility : 586.0 mg/ml ; 3.33 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.61

Safety of [ 106675-70-1 ]

Signal Word:Danger Class:9
Precautionary Statements:P260-P264-P273-P301+P312-P305+P351+P338-P314 UN#:3077
Hazard Statements:H302-H319-H372-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 106675-70-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 106675-70-1 ]

[ 106675-70-1 ] Synthesis Path-Downstream   1~85

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  • 2-Oxo-octanoic acid methylamide [ No CAS ]
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  • phenylmagnesium bromide [ No CAS ]
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  • phenylmagnesium bromide [ No CAS ]
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  • 22
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  • N-methoxy-N-methyl-2-oxo-2-(thiophen-2-yl)acetamide [ No CAS ]
  • 23
  • [ 109-72-8 ]
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  • 27
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  • N-Methyl-2-oxo-2-(2,4,6-trimethyl-phenyl)-acetamide [ No CAS ]
  • N-Methoxy-N-methyl-α-oxo-2',4',6'-trimethylbenzeneacetamide [ No CAS ]
  • 28
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  • N-Methyl-2-oxo-2-thiophen-2-yl-acetamide [ No CAS ]
  • N-methoxy-N-methyl-2-oxo-2-(thiophen-2-yl)acetamide [ No CAS ]
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  • [ 16750-63-3 ]
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  • N-Methoxy-N-methyl-α-oxo-2'-methoxybenzeneacetamide [ No CAS ]
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  • N-Methoxy-N-methyl-α-oxo-4'-methoxybenzeneacetamide [ No CAS ]
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  • n-butyl-MgX (X=halogen) [ No CAS ]
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  • 44
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  • n-hexyl-MgX (X=halogen) [ No CAS ]
  • 2-Oxo-octanoic acid methylamide [ No CAS ]
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  • 4-MePhMgX (X=halogen) [ No CAS ]
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  • 4-ClPhMgX (X=halogen) [ No CAS ]
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  • 47
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  • 49
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  • (4-hydroxy-3-methyl-5-oxo-5<i>H</i>-furan-2-ylidene)-acetic acid methyl ester [ No CAS ]
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  • 50
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  • (E)-4-Hydroxy-5'-methyl-4',5'-dihydro-[2,3']bifuranylidene-5,2'-dione [ No CAS ]
  • 51
  • [ 609-14-3 ]
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  • 2-(4-hydroxy-5-oxo-5<i>H</i>-furan-2-ylidene)-propionic acid ethyl ester [ No CAS ]
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  • (E)-4-Hydroxy-4',5'-dihydro-[2,3']bifuranylidene-5,2'-dione [ No CAS ]
  • 53
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  • tert-butyl [4-hydroxy-5-oxofuran-2(5H)-ylidene]acetate [ No CAS ]
  • 54
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  • 3-hydroxy-5-(2-oxo-2-phenyl-ethylidene)-5<i>H</i>-furan-2-one [ No CAS ]
  • 55
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  • 3-hydroxy-5-(2-oxo-cyclopentylidene)-5<i>H</i>-furan-2-one [ No CAS ]
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  • 2-(4-hydroxy-5-oxo-5<i>H</i>-furan-2-ylidene)-butyric acid ethyl ester [ No CAS ]
  • 57
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  • <i>N</i>,<i>N</i>-diethyl-2-(4-hydroxy-5-oxo-5<i>H</i>-furan-2-ylidene)-acetamide [ No CAS ]
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  • (E)-5'-Ethyl-4-hydroxy-4',5'-dihydro-[2,3']bifuranylidene-5,2'-dione [ No CAS ]
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  • 3-hydroxy-5-(2-oxo-cyclohexylidene)-5<i>H</i>-furan-2-one [ No CAS ]
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  • 1-propenylmagnesium chloride [ No CAS ]
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  • (4-hydroxy-5-oxo-5<i>H</i>-furan-2-ylidene)-thioacetic acid <i>S</i>-<i>tert</i>-butyl ester [ No CAS ]
  • (4-hydroxy-5-oxo-5<i>H</i>-furan-2-ylidene)-thioacetic acid <i>S</i>-<i>tert</i>-butyl ester [ No CAS ]
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  • 3-hydroxy-5-(2-oxo-cyclohexylidene)-5<i>H</i>-furan-2-one [ No CAS ]
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  • 3-hydroxy-5-(1-oxo-octahydro-naphthalen-2-ylidene)-5<i>H</i>-furan-2-one [ No CAS ]
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  • 3-hydroxy-5-(1-methyl-2-oxo-propylidene)-5<i>H</i>-furan-2-one [ No CAS ]
  • 3-hydroxy-5-(1-methyl-2-oxo-propylidene)-5<i>H</i>-furan-2-one [ No CAS ]
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  • 3-hydroxy-5-(2-oxo-propylidene)-5<i>H</i>-furan-2-one [ No CAS ]
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YieldReaction ConditionsOperation in experiment
87.9 - 96.0% Example 14 (Synthesis of N,N'-dimethoxy-N,N'-dimethyl oxamide) In a flask having an inner volume of 200 ml and equipped with a stirring device, a thermometer and a dropping funnel were charged 12.63 g (84.7 mmol) of 98% by weight diethyl oxalate, 16.72 g (169.4 mmol) of 98.8% by weight N,O-dimethylhydroxylamine hydrochloride and 10 ml of methanol, and while maintaining the liquid temperature to 3 to 7C, 65.36 g (338.8 mmol) of 28% by weight sodium methoxide-methanol solution was gradually added dropwise, and the resulting mixture was reacted at 3 to 8C for 3 hours under stirring. After completion of the reaction, in a flask having an inner volume of 300 ml and equipped with a stirring device, a thermometer and a dropping funnel was charged 90 ml (180 mmol) of 2 mol/l hydrochloric acid and the liquid was cooled to 5C. Then, the above-mentioned reaction mixture was gradually added dropwise to the liquid while maintaining the liquid temperature to 5 to 15C, and the resulting mixture was stirred. When this solution was analyzed (the absolute quantitative method) by high performance liquid chromatography, 13.25 g (Reaction yield: 88.8%) of N,N'-dimethoxy-N,N'-dimethyl oxamide was found to be formed.; Example 15 (Synthesis of N,N'-dimethoxy-N,N'-dimethyl oxamide) In a flask having an inner volume of 200 ml and equipped with a stirring device, a thermometer and a dropping funnel were charged 12.63 g (84.7 mmol) of 98% by weight diethyl oxalate, 16.72 g (169.4 mmol) of 98.8% by weight N,O-dimethylhydroxylamine hydrochloride and 10 ml of methanol, and while maintaining the liquid temperature to - 10 to -7C, 65.36 g (338.8 mmol) of 28% by weight sodium methoxide-methanol solution was gradually added dropwise to the mixture, and the resulting mixture was reacted at -9 to -7C for 3 hours under stirring. After completion of the reaction, in a flask having an inner volume of 300 ml and equipped with a stirring device, a thermometer and a dropping funnel was charged 90 ml (180 mmol) of 2 mol/l hydrochloric acid and the liquid was cooled to 5C. Then, while maintaining the liquid temperature to 5 to 15C, the above-mentioned reaction mixture was gradually added dropwise to the liquid and the resulting mixture was stirred. When this solution was analyzed (the absolute quantitative method) by high performance liquid chromatography, 13.12 g (Reaction yield: 87.9%) of N,N'-dimethoxy-N,N'-dimethyl oxamide was found to be formed.; Example 16 (Synthesis of N,N'-dimethoxy-N,N'-dimethyl oxamide) In a flask having an inner volume of 200 ml and equipped with a stirring device, a thermometer and a dropping funnel were charged, 12.63 g (84.7 mmol) of 98% by weight diethyl oxalate, 20.07 g (203.3 mmol) of 98.8% by weight N,O-dimethylhydroxylamine hydrochloride and 10 ml of methanol, and while maintaining the liquid temperature to 3 to 7C, 71.90 g (372.7 mmol) of 28% by weight sodium methoxide-methanol solution was gradually added dropwise to the mixture, and the resulting mixture was reacted at 3 to 7C for 3 hours under stirring. After completion of the reaction, in a flask having an inner volume of 300 ml and equipped with a stirring device, a thermometer and a dropping funnel was charged 110 ml (187 mmol) of 1.7 mol/l hydrochloric acid and the liquid was cooled to 5C. Then, while maintaining the liquid temperature to 5 to 15C, the above-mentioned reaction mixture was gradually added dropwise to the liquid and the resulting mixture was stirred. When this solution was analyzed (the absolute quantitative method) by high performance liquid chromatography, 14.32 g (Reaction yield: 96.0%) of N,N'-dimethoxy-N,N'-dimethyl oxamide was found to be formed.
86.4% The reaction was carried out in the same manner as in Example 2 except for changing 1.01 g (8.47 mmol) of 99% by weight dimethyl oxalate to 1.26 g (8.47 mmol) of 98% by weight diethyl oxalate, and changing methanol to ethanol in Example 2. As a result, 1.29 g (Reaction yield: 86.4%) of N,N'-dimethoxy-N,N'-dimethyl oxamide was found to be formed.
83.6% The reaction was carried out in the same manner as in Example 3 except for changing ethanol to tetrahydrofuran in Example 3. As a result, 1.25 g (Reaction yield: 83.6%) of N,N'-dimethoxy-N,N'-dimethyl oxamide was found to be formed.
80.8% The reaction was carried out in the same manner as in Example 3 except for changing ethanol to isopropyl alcohol in Example 3. As a result, 1.21 g (Reaction yield: 80.8%) of N,N'-dimethoxy-N,N'-dimethyl oxamide was found to be formed.
78.8% The reaction was carried out in the same manner as in Example 3 except for changing ethanol to acetonitrile in Example 3. As a result, 1.18 g (Reaction yield: 78.8%) of N,N'-dimethoxy-N,N'-dimethyl oxamide was found to be formed.
77.5% The reaction was carried out in the same manner as in Example 3 except for changing ethanol to dimethylformamide in Example 3. As a result, 1.16 g (Reaction yield: 77.5%) of N,N'-dimethoxy-N,N'-dimethyl oxamide was found to be formed.
75.7% The reaction was carried out in the same manner as in Example 3 except for changing ethanol to dimethylcarbonate in Example 3. As a result, 1.13 g (Reaction yield: 75.7%) of N,N'-dimethoxy-N,N'-dimethyl oxamide was found to be formed.
71.0% The reaction was carried out in the same manner as in Example 3 except for changing ethanol to toluene in Example 3. As a result, 1.05 g (Reaction yield: 71.0%) of N,N'-dimethoxy-N,N'-dimethyl oxamide was found to be formed.
61.6% In a flask having an inner volume of 1000 ml and equipped with a stirring device, a thermometer and a dropping funnel were charged 126.8 g (0.85 mol) of 98% by weight diethyl oxalate, 169.0 g (1.70 mol) of 98.1% by weight N,O-dimethylhydroxylamine hydrochloride and 100 ml of methanol, and while maintaining the liquid temperature to 5 to 10C, 656.0 g (3.40 mol) of 28% by weight sodium methoxide-methanol solution was gradually added dropwise to the mixture, and then reacted at the same temperature for 3 hours under stirring. After completion of the reaction, in a flask having an inner volume of 2000 ml and equipped with a stirring device, a thermometer and a dropping funnel were charged 107.1 g (1.79 mol) of acetic acid and 893 g of water and the mixture was cooled to 5C. Then, the above-mentioned reaction mixture was gradually added dropwise to the mixture while maintaining the liquid temperature to 5 to 15C, and the resulting mixture was stirred. Then, the reaction mixture was concentrated under reduced pressure, and the concentrate was extracted with 1500 ml of ethyl acetate. The obtained organic layer (ethyl acetate layer) was again concentrated under reduced pressure, 240 g of n-heptane was added to the residue, and the mixture was stirred for 30 minutes while the liquid temperature was maintained to 5 to 10C. The precipitated crystals were collected by filtration, washed with cooled n-heptane and dried under reduced pressure to give 92.3 g (Isolation yield: 61.6%) of N,N'-dimethoxy-N,N'-dimethyl oxamide as white crystal. Incidentally, physical properties of the N,N'-dimethoxy-N,N'-dimethyl oxamide were as follows. Melting point; 89.5 to 92.0C 1H-NMR (CDCl3, delta (ppm)); 3.24 (6H, s), 3.74 (6H, s)

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YieldReaction ConditionsOperation in experiment
57.1% The reaction was carried out in the same manner as in Example 2 except for changing 1.01 g (8.47 mmol) of 99% by weight dimethyl oxalate to 2.07 g (8.47 mmol) of 99% by weight diphenyl oxalate, and changing methanol to ethanol in Example 2. As a result, 0.85 g (Reaction yield: 57.1%) of N,N'-dimethoxy-N,N'-dimethyl oxamide was found to be formed.
  • 77
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YieldReaction ConditionsOperation in experiment
83.1% The reaction was carried out in the same manner as in Example 2 except for changing 1.01 g (8.47 mmol) of 99% by weight dimethyl oxalate to 1.73 g (8.47 mmol) of 99% by weight dibutyl oxalate, and changing methanol to ethanol in Example 2. As a result, 1.24 g (Reaction yield: 83.1%) of N,N'-dimethoxy-N,N'-dimethyl oxamide was found to be formed.
  • 78
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YieldReaction ConditionsOperation in experiment
80.9% In a flask having an inner volume of 25 ml and equipped with a stirring device, a thermometer and a dropping funnel were charged 1.01 g (8.47 mmol) of 99% by weight dimethyl oxalate, 1.68 g (16.94 mmol) of 98.1% by weight N,O-dimethylhydroxylamine hydrochloride and 1 ml of methanol, and while maintaining the liquid temperature to 5 to 10C, 6.54 g (33.88 mmol) of a 28% by weight sodium methoxide-methanol solution was gradually added dropwise, and the mixture was reacted at the same temperature for 3 hours under stirring. After completion of the reaction, in a flask having an inner volume of 25 ml and equipped with a stirring device, a thermometer and a dropping funnel was charged 10 ml (2.00 mmol) of 2 mol/l acetic acid and the liquid was cooled to 5C. Then, the above-mentioned reaction mixture was gradually added dropwise to the liquid while maintaining the liquid temperature to 5 to 15C, and the resulting mixture was stirred. When this solution was analyzed (the absolute quantitative method) by high performance liquid chromatography, 1.21 g (Reaction yield: 80.9%) of N,N'-dimethoxy-N,N'-dimethyl oxamide was found to be formed.
61.0% In a flask having an inner volume of 25 ml and equipped with a stirring device and a thermometer were charged 1.01 g (8.47 mmol) of 99% by weight dimethyl oxalate, 1.68 g (16.94 mmol) of 98.1% by weight N,O-dimethylhydroxylamine hydrochloride and 5 ml of dimethylsulfoxide, and while maintaining the liquid temperature to 5 to 25C, 1.93 g (33.88 mmol) of 95% by weight sodium methoxide powder was charged to the mixture by dividing the powder to several portions, and the resulting mixture was reacted at the same temperature for 1.5 hours under stirring. After completion of the reaction, in a flask having an inner volume of 25 ml and equipped with a stirring device, a thermometer and a dropping funnel was charged 10 ml (2.00 mmol) of 2 mol/l acetic acid and the liquid was cooled to 5C. Then, the above-mentioned reaction mixture was gradually added dropwise to the liquid while maintaining the liquid temperature to 5 to 15C, and the resulting mixture was stirred. When this solution was analyzed (the absolute quantitative method) by high performance liquid chromatography, 0.91 g (Reaction yield: 61.0%) of N,N'-dimethoxy-N,N'-dimethyl oxamide was found to be formed.
  • 79
  • [ 615-81-6 ]
  • [ 6638-79-5 ]
  • [ 106675-70-1 ]
YieldReaction ConditionsOperation in experiment
82.4% The reaction was carried out in the same manner as in Example 2 except for changing 1.01 g (8.47 mmol) of 99% by weight dimethyl oxalate to 1.49 g (8.47 mmol) of 99% by weight diisopropyl oxalate, and changing methanol to ethanol in Example 2. As a result, 1.23 g (Reaction yield: 82.4%) of N,N'-dimethoxy-N,N'-dimethyl oxamide was found to be formed.
  • 80
  • [ 79-37-8 ]
  • [ 1634-04-4 ]
  • [ 6638-79-5 ]
  • [ 106675-70-1 ]
YieldReaction ConditionsOperation in experiment
24.28 g (69%) In pyridine; dichloromethane; Step A N,N'-Dimethyl-N,N'-dimethoxy oxamide A mixture of 48.0 g (0.49 mol) of N,O-dimethylhydroxylamine HCl in 250 mL of 3:2 v/v CH2Cl2/pyridine was cooled to -78 C. and treated with 17.4 mL (0.2 mol) of oxalyl chloride maintaining the internal temperature at less than -70 C. The resulting mixture was allowed to warm to rt and stirred for 20 h. The reaction was quenched with 250 mL of sat'd NaCl and the quenched mixture was extracted with 3*400 mL of CH2Cl2. The extracts were combined, dried over MgSO4 and concentrated. Recrystallization from 250 mL of methyl t-butyl ether afforded 24.28 g (69%) of the title compound: 1H NMR (500 MHz) delta 3.25 (s, 6H), 3.75 (s, 6H).
  • 81
  • [ 17247-58-4 ]
  • [ 106675-70-1 ]
  • [ 106-93-4 ]
  • [ 300853-99-0 ]
YieldReaction ConditionsOperation in experiment
22.3 g (80%) With hydrogenchloride; potassium; magnesium; In tetrahydrofuran; Step B N-Methyl-N-methoxy 2-oxo-3-cyclobutyl propanamide A suspension of 4.86 g (0.20 mol) of magnesium turnings in 250 mL of THF was treated with 2.0 mL (0.022 mol) of 1,2-dibromoethane and then warmed until gas evolution from the surface of the Mg was visible. 15.2 mL (0.178 mol) of 1,2-dibromoethane was added at rate to maintain a gentle reflux. After the addition, the resulting mixture was heated at reflux for 30 min, then cooled to rt. Potassium (15.6 g, 0.40 mol) was added in ~1 g portions; the mixture was warmed until the potassium started to react and a fine black precipitate formed. This was repeated until all of the potassium was added to the reaction mixture. The resulting suspension of Mg was cooled to 0 C. The finely divided Mg was treated with 22.5 mL (0.20 mol) of bromomethylcyclobutane maintaining the internal temperature at <5 C. The resulting mixture was stirred cold for 1 h, then was treated with 26.40 g (0.15 mol) of N,N'-dimethyl-N,N'-dimethoxy oxamide (from EXAMPLE 19, Step A) in portions as a solid. The resulting mixture was stirred at 0 C. for 16 h. The reaction was poured onto a mixture of 100 mL conc. HCl and 500 g of ice under N2 atmosphere. The quenched mixture was extracted with 1.5 L of EtOAc. The extract was washed with 500 mL of sat'd NaCl, dried over MgSO4 and concentrated. Flash chromatography on 500 g of silica gel using 3:1 v/v hexanes/EtOAc as the eluant afforded 22.3 g (80%) of the title compound: 1H NMR (500 MHz) delta 1.66-1.76 (m, 2H), 1.82-1.98 (m, 2H), 2.12-2.22 (m, 2H), 2.74-2.84 (3H), 3.20 (s, 3H), 3.66 (s, 3H).
  • 82
  • [ 23062-42-2 ]
  • [ 106675-70-1 ]
  • [ 1160639-92-8 ]
YieldReaction ConditionsOperation in experiment
Step 2 Treatment of 7-2 with butyl lithium will result in metalation of the thiophene nng at the 2 -position with the carboxylate group serving to direct metalation as shown in intermediate 7-2a (See Organic Syntheses 1970, 50, 104, Organic Syntheses 1995, 72, 163) Addition of the Weinreb's amide derived from oxalic acid (Sibi et alJ Org Chem , 1995, 60, 5016, Nahm, S , Weinreb, S M Tetrahedron Lett 1981, 22, 3815-3818) to this lithium species will afford <n="116"/>ketone 7-3
  • 83
  • [ 106675-70-1 ]
  • [ 30897-90-6 ]
  • 2-(4-fluoro-2-methylphenyl)-N-methyl-N-(methoxy)-2-oxoacetamide [ No CAS ]
  • 84
  • [ 144-62-7 ]
  • [ 1117-97-1 ]
  • [ 106675-70-1 ]
YieldReaction ConditionsOperation in experiment
86% General procedure: A solution of NHMe(OMe) (0.360 g, 6.0 mmol) and benzoic acid (0.244 g, 2.0 mmol) was stirred in dry toluene (10 mL) at 0 C for 10 min. A solution of PCl3 (0.137 g, 1.0 mmol) in dry toluene (2 mL) was then added dropwise to the mixture. The mixture was warmed to r.t. slowly and then stirred at 60 C for 0.5 h. When the reaction was complete (TLC monitoring), the mixture was cooled to r.t. The mixture was then quenched with sat. NaHCO3 soln (20 mL) and extracted with EtOAc (3 × 10 mL). The combined organic layers were dried (anhyd MgSO4). The solvent was removed in vacuo.The product was purified by column chromatography (silica gel, petroleum ether-EtOAc, 3:2) to give pure 3a as a colorless oil; yield: 320 mg (97%).
  • 85
  • [ 17680-04-5 ]
  • [ 106675-70-1 ]
  • 2-(benzo[d][1,3]dioxol-5-yl)-N-methoxy-N-methyl-2-oxoacetamide [ No CAS ]
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