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Product Details of [ 6099-04-3 ]

CAS No. :6099-04-3 MDL No. :MFCD00004386
Formula : C10H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :LZPNXAULYJPXEH-AATRIKPKSA-N
M.W : 178.18 Pubchem ID :637668
Synonyms :

Calculated chemistry of [ 6099-04-3 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.1
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.6
TPSA : 46.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.81
Log Po/w (XLOGP3) : 2.37
Log Po/w (WLOGP) : 1.68
Log Po/w (MLOGP) : 1.59
Log Po/w (SILICOS-IT) : 1.73
Consensus Log Po/w : 1.84

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.58
Solubility : 0.467 mg/ml ; 0.00262 mol/l
Class : Soluble
Log S (Ali) : -2.99
Solubility : 0.183 mg/ml ; 0.00103 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.99
Solubility : 1.84 mg/ml ; 0.0103 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.83

Safety of [ 6099-04-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6099-04-3 ]

* 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.

  • Upstream synthesis route of [ 6099-04-3 ]
  • Downstream synthetic route of [ 6099-04-3 ]

[ 6099-04-3 ] Synthesis Path-Upstream   1~25

  • 1
  • [ 6099-04-3 ]
  • [ 26829-43-6 ]
YieldReaction ConditionsOperation in experiment
51%
Stage #1: With chloroformic acid ethyl ester; triethylamine In acetone at 0℃;
Stage #2: With sodium azide In water; acetone at 20℃;
Stage #3: With tributyl-amine; Diphenylmethane In toluene at 190 - 210℃;
Step 1: To a solution of 3-methoxycinnamic acid (11.0 g, 62 mmol) and triethylamine (12.5 g, 124 mmol) in acetone (80 mL) was added ethyl chloroformate (approximately 1.5 equivalents) dropwise at 0° C. After stirring at this temperature for 1 hour, aqueous NaN3 (6.40 g, 100 mmol in 35 mL H2O) was added dropwise and the reaction mixture was stirred for 16 hours at ambient temperature. Water (100 mL) was added to the mixture and volatiles were removed in vacuo. The resulting slurry was extracted with toluene (3.x.50 mL) and the organic layers were combined, dried over MgSO4, and filtered. The filtrate was added dropwise to a heated solution of diphenylmethane (50 mL) and tributylamine (30 mL) at 190° C. The toluene was removed by distillation during the addition. After complete addition, the reaction temperature was raised to 210° C. for 2 hours. Upon cooling, the precipitated product was collected by filtration, washed with hexane (2.x.50 mL), and dried to provide the desired product as a white solid (5.53 g, 51percent) (Nicolas Briet et al, Tetrahedron, 2002, 5761-5766). LC-MS, MS m/z 176 (M++H).
51%
Stage #1: With sodium azide; chloroformic acid ethyl ester; triethylamine In water; acetone at 0 - 20℃; for 17 h;
Stage #2: With tributyl-amine; Diphenylmethane In toluene at 190 - 210℃; for 2 h;
Step 1 of Example 2 Preparation of 6-Methoxy-2H-isoquinolin-l-one 6-Methoxy-2H-isoquinolin-1-one To a solution of 3-methoxy cinnamic acid (11.04 g, 62 mmol), triethylamine (12.52 g, 124 mmol) in acetone (80 mL) was added ethyl chloroformate dropwise at 0 C. After stirring at this temperature for 1 h, aqueous NaN3 (6.40 g, 100 mmol in 35 mL H20) was added dropwise and the reaction mixture was stirred for 16 h at the ambient temperature. Water (100 mL) was added to the mixture and the volatile was removed in vacuo. The resulting slurry was extracted with toluene (3X50 mL) and the combined organic layers were dried over MgS04. This dried solution was added dropwise to a heated solution of diphenylmethane (50 mL) and tributylamine (30 mL) at 190 C. The toluene was distilled off as added. After complete addition, the reaction temperature was raised to 210 C for 2 h. After cooling, the precipitated product was collected by filtration, washed with hexane (2X50 mL), dried to yield a white solid (5.53 g, 51percent), MS inlz 176 (M++H).
51%
Stage #1: With triethylamine In acetone at 0℃; for 1 h;
Stage #2: With sodium azide In acetone at 20℃; for 16 h;
Stage #3: at 190 - 210℃; for 2 h;
To a solution of 3-methoxy cinnamic acid (11.04 g, 62 mmol) and triethylamine (12.52 g, 124 mmol) in acetone (80 mL) was added ethyl chloroformate (approximately 1.5 equivalents) dropwise at 0° C. After stirring at this temperature for 1 h, aqueous NaN3 (6.40 g, 100 mmol in 35 mL H2O) was added dropwise and the reaction mixture was stirred for 16 h at the ambient temperature. Water (100 mL) was added to the mixture and the volatile was removed in vacuo. The resulting slurry was extracted with toluene (3.x.50 mL) and the combined organic layers were dried over MgSO4. This dried solution was added dropwise to a heated solution of diphenylmethane (50 mL) and tributylamine (30 mL) at 190° C. The toluene was distilled off as added. After complete addition, the reaction temperature was raised to 210° C. for 2 h. After cooling, the precipitated product was collected by filtration, washed with hexane (2.x.50 mL), and dried to yield the desired product as a white solid (5.53 g, 51percent) (Nicolas Briet at el., Tetrahedron, 2002, 5761-5766). LC-MS (retention time: 0.82 min, method B), MS m/z 176 (M++H).
Reference: [1] Patent: US2009/285773, 2009, A1, . Location in patent: Page/Page column 12
[2] Patent: WO2005/46712, 2005, A1, . Location in patent: Page/Page column 57; 58
[3] Patent: US2005/143316, 2005, A1, . Location in patent: Page/Page column 34
[4] Patent: US2013/115190, 2013, A1,
[5] Patent: US2015/376233, 2015, A1,
[6] Patent: US9527885, 2016, B2,
[7] Patent: US2013/142754, 2013, A1,
  • 2
  • [ 6099-04-3 ]
  • [ 541-41-3 ]
  • [ 26829-43-6 ]
YieldReaction ConditionsOperation in experiment
51%
Stage #1: With triethylamine In acetone at 0℃; for 1 h;
Stage #2: With sodium azide In water; acetone at 20℃; for 16 h;
To a solution of 3-methoxy cinnamic acid (11.04 g, 62 mmol) and triethylamine (12.52 g, 124 mmol) in acetone (80mL) was added ethyl chloroformate (approximately 1.5 equivalents) dropwise at 0 C. After stirring at this temperature for 1 h, aqueous NaN3 (6.40 g, 100 mmol in 35 mLH20) was added dropwise and the reaction mixture was stirred for 16 h at the ambient temperature. Water (100 mL) was added to the mixture and the volatile was removed in vacuo. The resulting slurry was extracted with toluene (3X50 mL) and the combined organic layers were dried overMgS04. This dried solution was added dropwise to a heated solution of diphenylmethane (50 mL) and tributylamine (30 mL) at 190 C. The toluene was distilled off as added. After complete addition, the reaction temperature was raised to 210 C for 2 h. After cooling, the precipitated product was collected by filtration, washed with hexane (2X50 mL), and dried to yield the desired product as a white solid (5.53 g,51percent) (Nicolas Briet at el, Tetrahedron, 2002,5761-5766). LC-MS (retention time: 0.82 min, method B), MS m/z 176 (M++H).
51%
Stage #1: With triethylamine In acetone at 0℃; for 1 h;
Stage #2: With sodium azide In water; acetone at 20℃; for 16 h;
Stage #3: With tributyl-amine In Diphenylmethane at 190 - 210℃; for 2 h;
Compound 1 Isomers; N-(4,6-dimethyl-2-pyridinyl)-L-valyl-(4R)-N-((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)-4-((6-methoxy-1-isoquinolinyl)oxy)-L-prolinamide and N-(4,6-dimethyl-2-pyridinyl)-D-valyl-(4R)-N-((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)-4-((6-methoxy-1-isoquinolinyl)oxy)-L-prolinamide; Example 1; Preparation of Compounds 1A and 1B; Step 1:; To a solution of 3-methoxycinnamic acid (11.0 g, 62 mmol) and triethylamine (12.5 g, 124 mmol) in acetone (80 mL) was added ethyl chloroformate (approximately 1.5 equivalents) dropwise at 0° C. After stirring at this temperature for 1 hour, aqueous NaN3 (6.40 g, 100 mmol in 35 mL H2O) was added dropwise and the reaction mixture was stirred for 16 hours at ambient temperature. Water (100 mL) was added to the mixture and volatiles were removed in vacuo. The resulting slurry was extracted with toluene (3.x.50 mL) and the organic layers were combined, dried over MgSO4, and filtered. The filtrate was added dropwise to a heated solution of diphenylmethane (50 mL) and tributylamine (30 mL) at 190° C. The toluene was removed by distillation during the addition. After complete addition, the reaction temperature was raised to 210° C. for 2 hours. Upon cooling, the precipitated product was collected by filtration, washed with hexane (2.x.50 mL), and dried to provide the desired product as a white solid (5.53 g, 51percent) (Nicolas Briet et al, Tetrahedron, 2002, 5761-5766). LC-MS, MS m/z 176 (M++H).; Example 412; Preparation of IntermediatesExample of preparations of P2 isoquinoline intermediates for incorporation into compounds of Formula 1; Step 1:; To a solution of 3-methoxy cinnamic acid (11.04 g, 62 mmol) and triethylamine (12.52 g, 124 mmol) in acetone (80 mL) was added ethyl chloroformate (approximately 1.5 equivalents) dropwise at 0° C. After stirring at this temperature for 1 h, aqueous NaN3 (6.40 g, 100 mmol in 35 mL H2O; appropriate precautions must be taken when using sodium azide) was added dropwise and the reaction mixture was stirred for 16 h at the ambient temperature. Water (100 mL) was added to the mixture and the volatile was removed in vacuo. The resulting slurry was extracted with toluene (3.x.50 mL) and the combined organic layers were dried over MgSO4. This dried solution was added dropwise to a heated solution of diphenylmethane (50 mL) and tributylamine (30 mL) at 190° C. The toluene was distilled off as added. After complete addition, the reaction temperature was raised to 210° C. for 2 h. After cooling, the precipitated product was collected by filtration, washed with hexane (2.x.50 mL), and dried to yield the desired product as a white solid (5.53 g, 51percent) (Nicolas Briet at el, Tetrahedron, 2002, 5761-5766). MS m/z 176 (M++H).
33%
Stage #1: With triethylamine In acetone at 0℃; for 1 h;
Stage #2: With sodium azide In tributyl-amine; Diphenylmethane; water; acetone at 23 - 210℃; for 18 h;
Ethyl chloroformate (4.3 mL, 44.5 mmol) was added drop wise at 0 0C to a solution of 3-methoxy cinnamic acid (5.3 g, 29.7 mmol) and triethylamine (8.3 mL, 59.4 mmol) in acetone (35 mL). After 1 h at 0 0C, aqueous sodium azide (3.1 g, 47.5 mmol, 16 mL water) was added drop wise and the reaction mixture was stirred at 23 0C for 16 h. Water (50 mL) was added to the mixture and the volatile was removed under vacuo. The resulting slurry was extracted with toluene (3 x 25 mL) and the combined organic layers were dried (MgSO4). The dried solution was filtered and added drop wise at 190 0C to a solution of diphenylmethane (25 mL) and tributylamine (14.2 mL, 59.4 mmol). The toluene was distilled off as added. After complete addition, the reaction temperature was raised to 210 0C for 2 h. After cooling, the precipitated product was collected by filtration and washed with hexanes and dried under vacuum to yield 6-Methoxy-2H-isoquinolin-l-one (1.7 g, 9.7 mmol, 33percent yield). MS m/z 176 (Tv^+H).
Reference: [1] Patent: WO2003/99274, 2003, A1, . Location in patent: Page 92-93
[2] Patent: US2008/119461, 2008, A1, . Location in patent: Page/Page column 37; 134
[3] Patent: WO2007/5838, 2007, A2, . Location in patent: Page/Page column 55
  • 3
  • [ 6099-04-3 ]
  • [ 541-41-3 ]
  • [ 26829-43-6 ]
Reference: [1] Patent: US2009/203629, 2009, A1,
  • 4
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  • [ 26829-43-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 4, p. 1084 - 1088
[2] Patent: EP2314593, 2016, B1,
  • 5
  • [ 6099-04-3 ]
  • [ 10516-71-9 ]
YieldReaction ConditionsOperation in experiment
100% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 12 h; 3-methoxycinnamic acid (8) (3.56 g, 19.98 mmol) was dissolved in MeOH (100 mL), and 10percent Pd on carbon (0.44 g) was added. The mixture was stirred for 12 h at room temperature under H2 (balloon). The reaction mixture was then filtered through Celite®, and the Celite® was washed with EtOAc (3×30 mL). The filtrate (EtOAc and MeOH) was evaporated under reduced pressure resulting in carboxylic acid 10 (3.59 g, 19.7 mmol, quantitative). 1H NMR (CDCl3, 600 MHz) δ 11.93 (1H, s), 7.27 (1H, t, J=7.5 Hz), 6.88 (2H, m), 6.83 (1H, d, J=8 Hz), 3.79 (3H, s), 2.99 (2H, t, J=7 Hz), 2.73 (2H, t, J=7 Hz). 13C NMR (CDCl3, 150 MHz) δ 179.2, 159.9, 142.0, 129.6, 120.7, 114.2, 111.6, 54.9, 35.5, 30.6.
97% With palladium 10% on activated carbon; hydrogen In methanol Hydrogenation of 3-(3-methoxyphenyl)acrylic acid (1.0 g) over 10percent Pd/C (catalytic amount) in methanol (20 mL) gave 3-methoxy phenyl propanoic acid in 97percent yield, mp 43-46 °C, IR (KBr, v cm-1): 2920, 1708, 1593, 1436, 1313, 1208, 1156, 929, 686; 1H NMR (CDCl3, 300 MHz); δ 7.13 (t, 1H, Ar-H, J = 7.9, 7.7 Hz), 6.7 (m, 3H, Ar-H), 3.76 (s, 3H, OCH3), 2.86 (t, 2H, CH2, J = 7.9, 7.5 Hz), 2.52 (t, 2H, CH2, J = 7.9, 7.5 Hz), 13C NMR (CDCl3, 75 MHz): δ 179.3, 159.6, 141.7, 129.5, 120.5, 113.9, 111.6, 55, 35.5, 30.5. MS (ESI): m/z = 181 (M+H)+; HRMS: Calcd for C10H13O3: 181.08553. Found: 181.08592.
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[2] Patent: US2018/2355, 2018, A1, . Location in patent: Paragraph 0094
[3] Journal of Organic Chemistry, 1992, vol. 57, # 4, p. 1262 - 1271
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[15] Russian Chemical Bulletin, 2011, vol. 60, # 1, p. 63 - 68
  • 6
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  • 7
  • [ 2398-37-0 ]
  • [ 79-10-7 ]
  • [ 6099-04-3 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With potassium <i>tert</i>-butylate In water at 20℃; for 0.166667 h; Inert atmosphere; Green chemistry
Stage #2: With bis-(1-methylimidazole)palladium(II) dichloride In water at 100℃; for 12 h; Green chemistry
General procedure: Under a N2 atmosphere, LiOtBu or KOtBu (3.0 mmol), H2O (2.0 mL) and acrylic acid (1.2 mmol) were added into a Schlenk reaction tube and the mixture was stirred at room temperature for 10 minutes. Then an aryl halide 2 (1.0 mmol) and Pd(II)–Im complex 1 (1.0 molpercent) were added. The mixture was stirred at 100 °C for 12 h. After cooling to room temperature, the reaction mixture was acidified by HCl (4 M) to pH 1 and extracted with EtOAc. The organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was evaporated in vacuo and the residue was purified by flash chromatography on silica gel to afford the pure product 5.
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[2] Journal of Chemical Research, 2013, vol. 37, # 5, p. 294 - 297
  • 8
  • [ 33877-04-2 ]
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YieldReaction ConditionsOperation in experiment
72% With lithium hydroxide monohydrate In methanol for 2 h; Reflux To a solution of unsaturated ethyl ester (0.850 g, 4.33 mmol) in MeOH was added LiOH-H2O (0.730 g, 17.3 mmol). After reflux for 2h, 1M HCl aq. and AcOEt were added to the mixture. The organic layer was washed with H2O and brine. The solvent was evaporated in vacuo to yield unsaturated carboxylic acid (0.620 g, 3.73 mmol, 72percent) as a white powder. 1H NMR (400 MHz, CDCl3) δ: 3.84 (3H, s), 6.43 (1H, d, J=16.0 Hz), 6.96 (1H, dd, J=6.0, 2.4 Hz), 7.07 (1H, s), 7.14 (1H, d, J=8.0 Hz), 7.32 (1H, t, J=8.0 Hz), 7.75 (1H, d, J=16.0 Hz).
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  • 9
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[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 6, p. 1241 - 1254
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  • 11
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  • 12
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[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 6, p. 1241 - 1254
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  • 14
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  • 15
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[ 5676-64-2 ]

(Z)-3-(4-Methoxyphenyl)acrylic acid

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Alkenes

Chemical Structure| 20767-04-8

[ 20767-04-8 ]

(E)-3-(3,5-Dimethoxyphenyl)acrylic acid

Similarity: 0.98

Chemical Structure| 16909-11-8

[ 16909-11-8 ]

3-(3,5-Dimethoxyphenyl)acrylic acid

Similarity: 0.98

Chemical Structure| 830-09-1

[ 830-09-1 ]

3-(4-Methoxyphenyl)acrylic acid

Similarity: 0.97

Chemical Structure| 943-89-5

[ 943-89-5 ]

(E)-3-(4-Methoxyphenyl)acrylic acid

Similarity: 0.97

Chemical Structure| 5676-64-2

[ 5676-64-2 ]

(Z)-3-(4-Methoxyphenyl)acrylic acid

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Ethers

Chemical Structure| 20767-04-8

[ 20767-04-8 ]

(E)-3-(3,5-Dimethoxyphenyl)acrylic acid

Similarity: 0.98

Chemical Structure| 16909-11-8

[ 16909-11-8 ]

3-(3,5-Dimethoxyphenyl)acrylic acid

Similarity: 0.98

Chemical Structure| 830-09-1

[ 830-09-1 ]

3-(4-Methoxyphenyl)acrylic acid

Similarity: 0.97

Chemical Structure| 943-89-5

[ 943-89-5 ]

(E)-3-(4-Methoxyphenyl)acrylic acid

Similarity: 0.97

Chemical Structure| 5676-64-2

[ 5676-64-2 ]

(Z)-3-(4-Methoxyphenyl)acrylic acid

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Carboxylic Acids

Chemical Structure| 20767-04-8

[ 20767-04-8 ]

(E)-3-(3,5-Dimethoxyphenyl)acrylic acid

Similarity: 0.98

Chemical Structure| 16909-11-8

[ 16909-11-8 ]

3-(3,5-Dimethoxyphenyl)acrylic acid

Similarity: 0.98

Chemical Structure| 830-09-1

[ 830-09-1 ]

3-(4-Methoxyphenyl)acrylic acid

Similarity: 0.97

Chemical Structure| 943-89-5

[ 943-89-5 ]

(E)-3-(4-Methoxyphenyl)acrylic acid

Similarity: 0.97

Chemical Structure| 5676-64-2

[ 5676-64-2 ]

(Z)-3-(4-Methoxyphenyl)acrylic acid

Similarity: 0.97