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Product Details of [ 21080-81-9 ]

CAS No. :21080-81-9 MDL No. :MFCD11217157
Formula : C9H11NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :XMKHEATVFWAIMD-UHFFFAOYSA-N
M.W : 181.19 Pubchem ID :55251041
Synonyms :

Calculated chemistry of [ 21080-81-9 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.56
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.06
TPSA : 52.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.47
Log Po/w (XLOGP3) : 1.5
Log Po/w (WLOGP) : 1.67
Log Po/w (MLOGP) : 0.98
Log Po/w (SILICOS-IT) : 1.97
Consensus Log Po/w : 1.72

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.93
Solubility : 2.13 mg/ml ; 0.0118 mol/l
Class : Very soluble
Log S (Ali) : -2.21
Solubility : 1.13 mg/ml ; 0.00621 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.32
Solubility : 0.871 mg/ml ; 0.00481 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.77

Safety of [ 21080-81-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 21080-81-9 ]

* 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 [ 21080-81-9 ]
  • Downstream synthetic route of [ 21080-81-9 ]

[ 21080-81-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 21080-81-9 ]
  • [ 110256-15-0 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: at 20℃; for 72 h;
Stage #2: With hydrogenchloride In water
INTERMEDIATE 16 - PREPARATION OF 5-Cyclopropylisoxazole-3-carboxylic acid.; The mixture of ethyl 5-cyclopropylisoxazole-3-carboxylate (0.550 g; 3.04 mmol) and 1 M aqueous sodium hydroxide (9.1 1 ml
9.11 mmol) was stirred at room temperature during the weekend (72 h). The pH of the solution was adjusted to 1 by addition of 6N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate and was evaporated to furnish 0.446 g (96percent) of 5- cyclopropylisoxazole-3-carboxylic acid as a solid. ESI/APCI(+): 154 (M+H), 176 (M+Na).ESI/APCK-): 152 (M-H).
93%
Stage #1: With sodium hydroxide In methanol; water at 15 - 25℃; for 3 h;
Stage #2: With hydrogenchloride In water
Sodium ethoxide (10 g, 147 mmol) is combined with absolute EtOH (60 mL) in an oven-dried flask, under nitrogen and heated to 70° C. to aid dissolution. The mixture is cooled to 0° C., treated drop-wise with a mixture of cyclopropyl methyl ketone (14.56 mL, 147 mmol) and diethyl oxylate (19.96 mL, 147 mmol) and warmed to RT. Stirring was difficult, so additional EtOH (60 mL) is added and the mixture is stirred for 1 h, then heated to 80° C. for 45 min. The mixture is cooled to RT and concentrated to dryness. The resulting solid is triturated with EtOAc, filtered, and rinsed with EtOAc and Et2O to remove the reddish color. The solid is dissolved in water (300 mL), acidified to pH 2 with dilute H2SO4, extracted with Et2O (400 mL total), dried (Na2SO4) and concentrated to afford 18.0 g (66percent yield) of ethyl 4-cyclopropyl-2,4-dioxobutanoate as an amber oil. HRMS (ESI) calcd for C9H12O4 +H: 185.0814, found 185.0821 (M+H)+. Ethyl 4-cyclopropyl-2,4-dioxobutanoate (12.92 g, 70.1 mmol) is combined with hydroxylamine hydrochloride (14.62 g, 210.4 mmol) in EtOH (250 mL), heated to reflux for 1 h, cooled, and concentrated to dryness. The residue is partitioned between H2O (250 mL) and EtOAc (2.x.250 mL) and the combined organics are dried (MgSO4) and concentrated to an amber oil (13.89 g). The crude material is chromatographed over 500 g silica gel, eluting with 25percent EtOAc/hexane. The appropriate fractions are combined and concentrated to afford 10.71 g (84percent yield) of ethyl 5-cyclopropylisoxazole-3-carboxylate as a yellow oil. MS (CI) m/z: 182 (M+H)+. Sodium hydroxide (1.76 g, 44.0 mmol) in H2O (5 mL) is added to a solution of ethyl 5-cyclopropylisoxazole-3-carboxylate (1.97 g, 10.9 mmol) in MeOH (10 mL). The mixture is stirred at RT for 3 h, concentrated to remove the MeOH, and acidified to pH 2 with 5percent HCl. The acid is extracted with CH2Cl2 (6.x.20 mL), dried (MgSO4) and concentrated to afford 1.56 g (93percent yield) of 5-cyclopropylisoxazole-3-carboxylic acid as a white solid. MS (Cl) m/z: 154 (M+H)+. 5-Cyclopropylisoxazole-3-carboxylic acid (1.53 g, 10 mmol) is dissolved in benzene (30 mL), treated with oxalyl chloride (3.46 mL, 40 mmol) and heated to reflux for 2 h. The mixture is cooled, concentrated to dryness and the residual benzene is azeotroped off with CH2Cl2. The resulting acid chloride is dissolved in Me2CO (15 mL) and treated with a solution of NaN3 (1.95 g, 30 mmol) in H2O (7 mL). The mixture is vigorously stirred for 1 h, concentrated to remove the Me2CO, triturated with H2O, filtered, rinsed with water and dried under vacuum to afford 1.76 g (99percent yield) of 5-cyclopropylisoxazole-3-carbonyl azide as an off-white solid. 1H NMR (CDCl3, 400 MHz): δ 1.02, 1.14, 2.10, 6.35 ppm. 5-Cyclopropylisoxazole-3-carbonyl azide (447 mg, 2.5 mmol) is combined with 5-chloro-2,4-dimethoxyaniline (471 mg, 2.5 mmol) in anhydrous MeCN (30 mL) and heated to reflux for 18 h. The mixture is cooled and the resulting solid is filtered, rinsed with Et2O and dried in a vacuum oven to afford 619 mg (73percent yield) of Example 621 as a very light purple solid. HRMS (ESI) calcd for C15H16N3O4Cl +H: 338.0907, found 338.0896 (M+H)+.
93% With sodium hydroxide In water at 20℃; for 1 h; Into a 10-L round-bottom flask was placed ethyl 5-cyclopropylisoxazole-3- carboxylate (280 g, 1.55 mol, 1.00 equiv) and a solution of sodium hydroxide (74.3 g, 1.20 equiv) in water (4 L). The resulting solution was stirred for 1 h at room temperature. The resulting mixture was washed with ether. The pH value of the aqueous solution was adjusted to 2-3 with hydrochloric acid (12N). The resulting solution was extracted with ethyl acetate and the organic layers combined and concentrated under vacuum. This resulted in 220 g (93percent>) of 5-cyclopropylisoxazole-3-carboxylic acid as an off- white solid. LCMS (method A, ESI): RT = 1.99 min, m z = 153.9 [M+H]+. 1H-NMR (300 MHz CDCls): 8.42(brs, 1H), 6.37(s, 1H), 2.16-2.05(m, 1H), 1.29-1.12(m, 2H), 1.12-0.99(m, 2H) ppm.
93% at 20℃; for 1 h; Into a 10-L round-bottom flask was placed ethyl 5-cyclopropylisoxazole-3- carboxylate (280 g, 1.55 mol, 1.00 equiv) and a solution of sodium hydroxide (74.3 g, 1.20 equiv) in water (4 L). The resulting solution was stirred for 1 h at room temperature. The resulting mixture was washed with ether. The pH value of the aqueous solution was adjusted to 2-3 with hydrochloric acid (12N). The resulting solution was extracted with ethyl acetate and the organic layers combined and concentrated under vacuum. This resulted in 220 g (93percent) of 5-cyclopropylisoxazole-3-carboxylic acid as an off- white solid. 1H-NMR (300 MHz CDC13): δ 8.42 (brs, 1H), 6.37 (s, 1H), 2.16-2.05 (m, 1H), 1.29-1.12 (m, 2H), 1.12-0.99 (m, 2H); LCMS m/z = 153.9 [M+H]+.
93% at 20℃; for 1 h; [0266] Into a 10-L round-bottom flask was placed ethyl 5-cyclopropylisoxazole-3- carboxylate (280 g, 1.55 mol, 1.00 equiv) and a solution of sodium hydroxide (74.3 g, 1.20 equiv) in water (4 L). The resulting solution was stirred for 1 h at room temperature. The resulting mixture was washed with ether. The pH value of the aqueous solution was adjusted to 2-3 with hydrochloric acid (12N). The resulting solution was extracted with ethyl acetate and the organic layers combined and concentrated under vacuum. This resulted in 220 g (93percent>) of 5-cyclopropylisoxazole-3-carboxylic acid as an off- white solid. 1H-NMR (300 MHz CDC13): δ 8.42 (brs, 1H), 6.37 (s, 1H), 2.16-2.05 (m, 1H), 1.29-1.12 (m, 2H), 1.12-0.99 (m, 2H); LCMS m z = 153.9 [M+H]+.
93% With sodium hydroxide In water at 20℃; for 1 h; Into a 10-L round-bottom flask was placed ethyl 5-cyclopropylisoxazole-3- carboxylate (280 g, 1.55 mol, 1.00 equiv) and a solution of sodium hydroxide (74.3 g, 1.20 equiv) in water (4 L). The resulting solution was stirred for 1 h at room temperature. The resulting mixture was washed with ether. The pH value of the aqueous solution was adjusted to 2-3 with hydrochloric acid (12N). The resulting solution was extracted with ethyl acetate and the organic layers combined and concentrated under vacuum. This resulted in 220 g (93percent>) of 5-cyclopropylisoxazole-3-carboxylic acid as an off- white solid. LCMS (method A, ESI): RT = 1.99 min, m/z = 153.9 [M+H]+. 1H-NMR (300 MHz CDCls): 8.42(brs, 1H), 6.37(s, 1H), 2.16-2.05(m, 1H), 1.29-1.12(m, 2H), 1.12-0.99(m, 2H) ppm.
93% at 20℃; for 1 h; Into a 10-L round-bottom flask was placed ethyl 5-cyclopropylisoxazole-3- carboxylate (280 g, 1.55 mol, 1.00 equiv) and a solution of sodium hydroxide (74.3 g, 1.20 equiv) in water (4 L). The resulting solution was stirred for 1 h at room temperature. The resulting mixture was washed with ether. The pH value of the aqueous solution was adjusted to 2-3 with hydrochloric acid (12N). The resulting solution was extracted with ethyl acetate and the organic layers combined and concentrated under vacuum. This resulted in 220 g (93percent) of 5-cyclopropylisoxazole-3-carboxylic acid as an off-white solid. LCMS (method A, ESI): RT = 1.99 min, m/z = 153.9 [M+H]+. 1H-NMR (300 MHz CDCl3): 8.42(brs, 1H), 6.37(s, 1H), 2.16-2.05(m, 1H), 1.29-1.12(m, 2H), 1.12-0.99(m, 2H) ppm.

Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 1, p. 358 - 373
[2] Patent: WO2010/142801, 2010, A1, . Location in patent: Page/Page column 151
[3] Patent: US2003/236287, 2003, A1, . Location in patent: Page 46, 47
[4] Patent: WO2016/40502, 2016, A1, . Location in patent: Page/Page column 65
[5] Patent: WO2016/40504, 2016, A1, . Location in patent: Paragraph 0194
[6] Patent: WO2016/40498, 2016, A1, . Location in patent: Paragraph 0266
[7] Patent: WO2016/40511, 2016, A1, . Location in patent: Paragraph 0116
[8] Patent: WO2016/40515, 2016, A1, . Location in patent: Paragraph 0267
  • 2
  • [ 21080-80-8 ]
  • [ 21080-81-9 ]
YieldReaction ConditionsOperation in experiment
84% With hydroxylamine hydrochloride In ethanol for 1 h; Heating / reflux Sodium ethoxide (10 g, 147 mmol) is combined with absolute EtOH (60 mL) in an oven-dried flask, under nitrogen and heated to 70° C. to aid dissolution. The mixture is cooled to 0° C., treated drop-wise with a mixture of cyclopropyl methyl ketone (14.56 mL, 147 mmol) and diethyl oxylate (19.96 mL, 147 mmol) and warmed to RT. Stirring was difficult, so additional EtOH (60 mL) is added and the mixture is stirred for 1 h, then heated to 80° C. for 45 min. The mixture is cooled to RT and concentrated to dryness. The resulting solid is triturated with EtOAc, filtered, and rinsed with EtOAc and Et2O to remove the reddish color. The solid is dissolved in water (300 mL), acidified to pH 2 with dilute H2SO4, extracted with Et2O (400 mL total), dried (Na2SO4) and concentrated to afford 18.0 g (66percent yield) of ethyl 4-cyclopropyl-2,4-dioxobutanoate as an amber oil. HRMS (ESI) calcd for C9H12O4 +H: 185.0814, found 185.0821 (M+H)+. Ethyl 4-cyclopropyl-2,4-dioxobutanoate (12.92 g, 70.1 mmol) is combined with hydroxylamine hydrochloride (14.62 g, 210.4 mmol) in EtOH (250 mL), heated to reflux for 1 h, cooled, and concentrated to dryness. The residue is partitioned between H2O (250 mL) and EtOAc (2.x.250 mL) and the combined organics are dried (MgSO4) and concentrated to an amber oil (13.89 g). The crude material is chromatographed over 500 g silica gel, eluting with 25percent EtOAc/hexane. The appropriate fractions are combined and concentrated to afford 10.71 g (84percent yield) of ethyl 5-cyclopropylisoxazole-3-carboxylate as a yellow oil. MS (CI) m/z: 182 (M+H)+. Sodium hydroxide (1.76 g, 44.0 mmol) in H2O (5 mL) is added to a solution of ethyl 5-cyclopropylisoxazole-3-carboxylate (1.97 g, 10.9 mmol) in MeOH (10 mL). The mixture is stirred at RT for 3 h, concentrated to remove the MeOH, and acidified to pH 2 with 5percent HCl. The acid is extracted with CH2Cl2 (6.x.20 mL), dried (MgSO4) and concentrated to afford 1.56 g (93percent yield) of 5-cyclopropylisoxazole-3-carboxylic acid as a white solid. MS (Cl) m/z: 154 (M+H)+. 5-Cyclopropylisoxazole-3-carboxylic acid (1.53 g, 10 mmol) is dissolved in benzene (30 mL), treated with oxalyl chloride (3.46 mL, 40 mmol) and heated to reflux for 2 h. The mixture is cooled, concentrated to dryness and the residual benzene is azeotroped off with CH2Cl2. The resulting acid chloride is dissolved in Me2CO (15 mL) and treated with a solution of NaN3 (1.95 g, 30 mmol) in H2O (7 mL). The mixture is vigorously stirred for 1 h, concentrated to remove the Me2CO, triturated with H2O, filtered, rinsed with water and dried under vacuum to afford 1.76 g (99percent yield) of 5-cyclopropylisoxazole-3-carbonyl azide as an off-white solid. 1H NMR (CDCl3, 400 MHz): δ 1.02, 1.14, 2.10, 6.35 ppm. 5-Cyclopropylisoxazole-3-carbonyl azide (447 mg, 2.5 mmol) is combined with 5-chloro-2,4-dimethoxyaniline (471 mg, 2.5 mmol) in anhydrous MeCN (30 mL) and heated to reflux for 18 h. The mixture is cooled and the resulting solid is filtered, rinsed with Et2O and dried in a vacuum oven to afford 619 mg (73percent yield) of Example 621 as a very light purple solid. HRMS (ESI) calcd for C15H16N3O4Cl +H: 338.0907, found 338.0896 (M+H)+.
66.3% With hydroxylamine hydrochloride In ethanol at 20 - 80℃; for 2 h; Into a 10 L round-bottom flask, was placed a solution of ethyl 4-cyclopropyl-2,4- dioxobutanoate (177 g) in ethanol (1.1 L) and NH2OH-HCl (200 g). The resulting solution was stirred for 1 h at 20-30°C. The resulting solution was allowed to react, with stirring, for an additional 1 h at 80°C. The resulting mixture was concentrated under vacuum. The residue was purified on a silica gel column with ethyl acetate/petroleum ether (1/10). This resulted in 143 g (the two step yield was 66.3percent) of ethyl 5- cyclopropylisoxazole-3-carboxylate as a yellow oil. TLC (ethyl acetate/petroleum ether = l/5): Rf = 0.2.
143 mg With hydroxylamine hydrochloride In ethanol; water at 20 - 80℃; for 2 h; Into a 10 L round-bottom flask, was placed a solution of ethyl 4-cyclopropyl-2,4- dioxobutanoate (177 g) in ethanol (1.1 L) and NH2OH-HCl (200 g). The resulting solution was stirred for 1 h at 20-30°C. The resulting solution was allowed to react, with stirring, for an additional 1 h at 80°C. The resulting mixture was concentrated under vacuum. The residue was purified on a silica gel column with ethyl acetate/petroleum ether (1/10). This resulted in 143 g (the two step yield was 66.3percent) of ethyl 5- cyclopropylisoxazole-3-carboxylate as a yellow oil. TLC (ethyl acetate/petroleum ether =1/5): Rf = 0.2.
143 g With hydroxylamine hydrochloride In ethanol at 20 - 80℃; for 2 h; Into a 10 L round-bottom flask, was placed a solution of ethyl 4-cyclopropyl-2,4- dioxobutanoate (177 g) in ethanol (1.1 L) and NH2OH-HCl (200 g). The resulting solution was stirred for 1 h at 20-30 °C. The resulting solution was allowed to react, with stirring, for an additional 1 h at 80°C. The resulting mixture was concentrated under vacuum. The residue was purified on a silica gel column with ethyl acetate/petroleum ether (1/10). This resulted in 143 g (the two step yield was 66.3percent) of ethyl 5- cyclopropylisoxazole-3-carboxylate as a yellow oil. TLC (ethyl acetate/petroleum ether =1/5): Rf = 0.2.
143 g With hydroxylamine hydrochloride In ethanol at 20 - 30℃; for 2 h; [0265] Into a 10 L round-bottom flask, was placed a solution of ethyl 4-cyclopropyl-2,4- dioxobutanoate (177 g) in ethanol (1.1 L) and NH2OH-HCl (200 g). The resulting solution was stirred for 1 h at 20-30 °C. The resulting solution was allowed to react, with stirring, for an additional 1 h at 80°C. The resulting mixture was concentrated under vacuum. The residue was purified on a silica gel column with ethyl acetate/petroleum ether (1/10). This resulted in 143 g (the two step yield was 66.3percent) of ethyl 5- cyclopropylisoxazole-3-carboxylate as a yellow oil. TLC (ethyl acetate/petroleum ether = l/5): Rf = 0.2.
143 g With hydroxylamine hydrochloride In ethanol at 20 - 80℃; for 2 h; Into a 10 L round-bottom flask, was placed a solution of ethyl 4-cyclopropyl-2,4- dioxobutanoate (177 g) in ethanol (1.1 L) and NH2OH-HCl (200 g). The resulting solution was stirred for 1 h at 20-30oC. The resulting solution was allowed to react, with stirring, for an additional 1 h at 80oC. The resulting mixture was concentrated under vacuum. The residue was purified on a silica gel column with ethyl acetate/petroleum ether (1/10). This resulted in 143 g (the two step yield was 66.3percent) of ethyl 5- cyclopropylisoxazole-3-carboxylate as a yellow oil. TLC (ethyl acetate/petroleum ether =1/5): Rf = 0.2.

Reference: [1] Patent: US2003/236287, 2003, A1, . Location in patent: Page 46, 47
[2] Patent: WO2016/40511, 2016, A1, . Location in patent: Paragraph 0115
[3] Patent: WO2016/40502, 2016, A1, . Location in patent: Page/Page column 65
[4] Patent: WO2016/40504, 2016, A1, . Location in patent: Paragraph 0193
[5] Patent: WO2016/40498, 2016, A1, . Location in patent: Paragraph 0265
[6] Patent: WO2016/40515, 2016, A1, . Location in patent: Paragraph 0266
  • 3
  • [ 626-35-7 ]
  • [ 6746-94-7 ]
  • [ 21080-81-9 ]
YieldReaction ConditionsOperation in experiment
92% With 1,4-diaza-bicyclo[2.2.2]octane In ethanol at 150℃; for 0.333333 h; Microwave irradiation INTERMEDIATE 15 - PREPARATION OF Ethyl δ-cyclopropylisoxazole-S-carboxylate.; A solution of ethynylcyclopropane (0.40 ml
4.58 mmol), ethyl 2-nitroacetate (1.30 ml
1 1.46 mmol), and 1 ,4-diazobicyclo[2.2.2]octane (DABCO, 0.053 g; 0.458 mmol) in ethanol(3 ml.) was irradiated in a microwave oven at 150 0C for 20 min and was then evaporated.The residue was dissolved in ethyl acetate and the solution was washed with water. The organic layer was evaporated and the residue was purified by flash chromatography on silica gel (eluent: 20 to 100percent of dichloromethane in heptane) to afford 0.765 g (92 percent) of ethyl 5-cyclopropylisoxazole-3-carboxylate as a yellow oil.ESI/APCI(+): 182 (M+H).
0.4 g With 1,4-diaza-bicyclo[2.2.2]octane In ethanol at 150℃; for 0.5 h; Inert atmosphere A mixture of ethyl 2-nitroacetate (1.0 g, 7.6 mmol, 2.5 eq), ethynylcyclopropane (0.2 g, 3.0 mmol, 1 eq),DABCO (33.9 mg, 303 imol, 0.1 eq) in 2 mL of EtOH was degassed and purged with N2 three times. The mixture was stirred at 150 °C for 30 mm under microwave condition. It was evaporated under reduced pressure to give a residue. The residue was purified by column chromatography (Si02 eluting with petroleum ether:ethyl acetate = 30:1) to give 0.4 g of ethyl 5 -cyclopropylisoxazole-3 -carboxylate as a colorless liquid.
Reference: [1] Patent: WO2010/142801, 2010, A1, . Location in patent: Page/Page column 151
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 27, p. 4643 - 4655
[3] Patent: WO2018/119395, 2018, A1, . Location in patent: Page/Page column 211; 212
  • 4
  • [ 765-43-5 ]
  • [ 95-92-1 ]
  • [ 21080-81-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6033 - 6047
  • 5
  • [ 1354822-96-0 ]
  • [ 21080-81-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 1, p. 358 - 373
  • 6
  • [ 765-43-5 ]
  • [ 21080-81-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 1, p. 358 - 373
[2] Patent: WO2016/40502, 2016, A1,
[3] Patent: WO2016/40504, 2016, A1,
[4] Patent: WO2016/40498, 2016, A1,
[5] Patent: WO2016/40511, 2016, A1,
[6] Patent: WO2016/40515, 2016, A1,
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