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Chemistry
Organic Building Blocks
Isoxazoles
chloromethyl
Ethyl 3-(chloromethyl)isoxazole-5-carboxylate
Chemistry
Organic Building Blocks
Heterocyclic Building Blocks
Isoxazoles
Chlorides Esters
chloromethyl

[ CAS No. 1141427-74-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

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Chemical Structure| 1141427-74-8
Chemical Structure| 1141427-74-8
Structure of 1141427-74-8 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 1141427-74-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 1141427-74-8 ]

Product Details of [ 1141427-74-8 ]

CAS No. :1141427-74-8 MDL No. :MFCD20637793
Formula : C7H8ClNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :HGMAUHFCWCICEY-UHFFFAOYSA-N
M.W : 189.60 Pubchem ID :89816484
Synonyms :

Calculated chemistry of [ 1141427-74-8 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.43
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.35
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) : -6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : 1.35
Log Po/w (WLOGP) : 1.44
Log Po/w (MLOGP) : 0.67
Log Po/w (SILICOS-IT) : 1.93
Consensus Log Po/w : 1.51

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.91
Solubility : 2.33 mg/ml ; 0.0123 mol/l
Class : Very soluble
Log S (Ali) : -2.05
Solubility : 1.69 mg/ml ; 0.00889 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.74
Solubility : 0.343 mg/ml ; 0.00181 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.46

Safety of [ 1141427-74-8 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H302-H314 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1141427-74-8 ]

* 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 [ 1141427-74-8 ]

[ 1141427-74-8 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 51451-05-9 ]
  • [ 623-47-2 ]
  • [ 1141427-74-8 ]
  • [ 1379165-76-0 ]
YieldReaction ConditionsOperation in experiment
1: 61% 2: 8% With sodium hypochlorite In tetrahydrofuran at 0 - 20℃;
Reference： [1]Lilienkampf, Annamaria; Jialin, Mao; Baojie, Wan; Yuehong, Wang; Franzblau, Scott G.; Kozikowski, Alan P. [Journal of Medicinal Chemistry, 2009, vol. 52, # 7, p. 2109 - 2118]
  • 2
  • [ 51451-05-9 ]
  • [ 623-47-2 ]
  • [ 1141427-74-8 ]
YieldReaction ConditionsOperation in experiment
12.2% Stage #1: chloroacetaldoxime; propynoic acid ethyl ester In tetrahydrofuran at 0℃; Stage #2: With sodium hypochlorite In tetrahydrofuran at 0 - 20℃; Step 2: To a stirred solution of compound 266 (40 g, 0.437 mol) in THF (150 mL) was added dropwise ethyl propiolate (50 mL, 0.5 mol) at 0 °C. NaOCI (10%, 1.5 L) was added dropwise to the above mixture at 0 °C. After the addition, the mixture was stirred at room temperature for 18 hours. The mixture was concentrated to remove THF, extracted with EtOAc (2 x 500 mL). The combined organic layers were washed with brine (200 mL x 3), dried over Na2S04, and concentrated to give a residue, which was purified by column chromatography over silica, gel. (Rf ~ 0.5, petroleum ether/EtOAc = 10:1 -5:1 ) to give compound 267 (1 1 g, 12.2 %) as a light yellow solid. 1H NMR (400 MHz, CDCI3) δ 7.05 (s, 1 H), 4.64 (s, 2H), 4.49-4.41 (m, 2H), 1 1.46-1.43 (t, 3H).
Reference： [1]Current Patent Assignee: PFIZER INC - WO2013/132376, 2013, A1 Location in patent: Page/Page column 232
  • 3
  • [ 1141427-74-8 ]
  • C5H5ClN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With ammonia In methanol at 0 - 20℃; Step 3: To a stirred solution of NH3 (g) in MeOH (12N, 100 mL) was added compound 267 (1 1 g, 0.058 mol) at 0 °C. After the addition, the mixture was stirred at room temperature for 10 minutess. TLC (Petroleum ether/EtOAc = 1 :1 ) indicated the reaction was complete. The mixture was concentrated to give a residue, which was purified by column chromatography over silica, gel (Rf = 0.2, petroleum ether/EtOAc = 1 :1-2:1 ) to give compound 268 (6.5 g, 70 %) as a white solid. 1H NMR (400 MHz, CDCI3) δ 7.06 (s, 1 H), 6.2 (s, 1 H), 5.74 (s, 1 H), 4.63 (s, 2H),
Reference： [1]Current Patent Assignee: PFIZER INC - WO2013/132376, 2013, A1 Location in patent: Page/Page column 232
  • 4
  • [ 1141427-74-8 ]
  • C6H9N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ammonia / methanol / 0 - 20 °C 2: tetrahydrofuran / 18 h / 110 °C
Reference： [1]Current Patent Assignee: PFIZER INC - WO2013/132376, 2013, A1
  • 5
  • [ 1141427-74-8 ]
  • C11H17N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ammonia / methanol / 0 - 20 °C 2: tetrahydrofuran / 18 h / 110 °C 3: triethylamine / tetrahydrofuran / 0 - 20 °C
Reference： [1]Current Patent Assignee: PFIZER INC - WO2013/132376, 2013, A1
  • 6
  • [ 1141427-74-8 ]
  • C11H15N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: ammonia / methanol / 0 - 20 °C 2: tetrahydrofuran / 18 h / 110 °C 3: triethylamine / tetrahydrofuran / 0 - 20 °C 4: trifluoroacetic anhydride; triethylamine / dichloromethane / 12 h / 0 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: PFIZER INC - WO2013/132376, 2013, A1
  • 7
  • [ 1141427-74-8 ]
  • 3-((methylamino)methyl)isoxazole-5-carbonitrile hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: ammonia / methanol / 0 - 20 °C 2: tetrahydrofuran / 18 h / 110 °C 3: triethylamine / tetrahydrofuran / 0 - 20 °C 4: trifluoroacetic anhydride; triethylamine / dichloromethane / 12 h / 0 °C / Inert atmosphere 5: hydrogenchloride / ethyl acetate / 2 h / 20 °C
Reference： [1]Current Patent Assignee: PFIZER INC - WO2013/132376, 2013, A1
  • 8
  • [ 1141427-74-8 ]
  • C19H16BrFN6O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: ammonia / methanol / 0 - 20 °C 2: tetrahydrofuran / 18 h / 110 °C 3: triethylamine / tetrahydrofuran / 0 - 20 °C 4: trifluoroacetic anhydride; triethylamine / dichloromethane / 12 h / 0 °C / Inert atmosphere 5: hydrogenchloride / ethyl acetate / 2 h / 20 °C 6: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / -35 - 20 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: PFIZER INC - WO2013/132376, 2013, A1
  • 9
  • [ 1141427-74-8 ]
  • (10R)-7-amino-12-fluoro-10,16-dimethyl-15-oxo-10,15,16,17-tetrahydro-8,4-(azeno)[1,2]oxazolo[4,3-h][2,5,11]benzoxadiazacyclotetradecine-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: ammonia / methanol / 0 - 20 °C 2: tetrahydrofuran / 18 h / 110 °C 3: triethylamine / tetrahydrofuran / 0 - 20 °C 4: trifluoroacetic anhydride; triethylamine / dichloromethane / 12 h / 0 °C / Inert atmosphere 5: hydrogenchloride / ethyl acetate / 2 h / 20 °C 6: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / -35 - 20 °C / Inert atmosphere 7: palladium diacetate; catacxium A; potassium acetate / tert-Amyl alcohol / 18 h / 120 °C
Reference： [1]Current Patent Assignee: PFIZER INC - WO2013/132376, 2013, A1
  • 10
  • [ 1141427-74-8 ]
  • C20H17BrFN5O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: ammonia / methanol / 0 - 20 °C 2: tetrahydrofuran / 18 h / 110 °C 3: triethylamine / tetrahydrofuran / 0 - 20 °C 4: trifluoroacetic anhydride; triethylamine / dichloromethane / 12 h / 0 °C / Inert atmosphere 5: hydrogenchloride / ethyl acetate / 2 h / 20 °C 6: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / -35 - 20 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: PFIZER INC - WO2013/132376, 2013, A1
  • 11
  • [ 1141427-74-8 ]
  • (10R)-7-amino-12-fluoro-10,16-dimethyl-15-oxo-10,15,16,17-tetrahydro-8,4-(metheno)[1,2]oxazolo[4,3-h][2,5,11]benzoxadiazacyclotetradecine-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: ammonia / methanol / 0 - 20 °C 2: tetrahydrofuran / 18 h / 110 °C 3: triethylamine / tetrahydrofuran / 0 - 20 °C 4: trifluoroacetic anhydride; triethylamine / dichloromethane / 12 h / 0 °C / Inert atmosphere 5: hydrogenchloride / ethyl acetate / 2 h / 20 °C 6: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / -35 - 20 °C / Inert atmosphere 7: palladium diacetate; catacxium A; potassium acetate / tert-Amyl alcohol / 18 h / 120 °C
Reference： [1]Current Patent Assignee: PFIZER INC - WO2013/132376, 2013, A1
  • 12
  • [ 51451-05-9 ]
  • [ 105-37-3 ]
  • [ 1141427-74-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hypochlorite In tetrahydrofuran Synthesis of compound 2h and 2i: To a round-bottom flask containing an aqueous solution of chloroacetaldehyde (0.3 mol / 47 mL), sodium acetate (0.3 mol) and hydroxylamine hydrochloride (0.3 mol) were added. Then the reaction mixture was stirred for 30 min. After extraction of the reaction mixture with EtOAc (3× 25 mL), the combined organic phases were washed with brine (20 mL) and dried over anhydrous Na2SO4. The solvent was removed in vacuo to furnish the crude intermediate compound. This residue was directly added to the solution of ethyl propionate (29.7 mg, 0.3 mmol) in anhydrous THF (5 mL). Subsequently, 10 mL of 10% sodium hypochlorite solution was added dropwise over 2 h, and the reaction mixture was stirred overnight. After cooling to room temperature, the reaction mixture was extracted with EtOAc (3 × 25 mL). The combined organic phases were washed with brine (20 mL) and dried over anhydrous Na2SO4. After filtration, the organic solvent was evaporated and the crude product was purified by automated flash chromatography using a gradient eluent from hexane to 20% EtOAc-hexane. The isoxazole product was then reacted with the corresponding 4-hydroxyquinoline using general procedure B for the preparation of compound 2h and 2i.
Reference： [1]Current Patent Assignee: DARTMOUTH COLLEGE - WO2017/136642, 2017, A1 Location in patent: Page/Page column 0158
  • 13
  • [ 306935-26-2 ]
  • [ 1141427-74-8 ]
  • 3-[[[8-trifluoromethoxy-2-trifluoromethyl-4-quinolinyl]oxy]methyl]-5-isoxazolecarboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 8-(trifluoromethoxyl)-2-(trifluoromethyl)-4-quinolinol With potassium carbonate In acetone for 1h; Reflux; Stage #2: 3-(chloromethyl)isoxazole-5-carboxylic acid ethyl ester With potassium iodide In acetone Reflux; Synthesis of compound 2h and 2i: To a round-bottom flask containing an aqueous solution of chloroacetaldehyde (0.3 mol / 47 mL), sodium acetate (0.3 mol) and hydroxylamine hydrochloride (0.3 mol) were added. Then the reaction mixture was stirred for 30 min. After extraction of the reaction mixture with EtOAc (3× 25 mL), the combined organic phases were washed with brine (20 mL) and dried over anhydrous Na2SO4. The solvent was removed in vacuo to furnish the crude intermediate compound. This residue was directly added to the solution of ethyl propionate (29.7 mg, 0.3 mmol) in anhydrous THF (5 mL). Subsequently, 10 mL of 10% sodium hypochlorite solution was added dropwise over 2 h, and the reaction mixture was stirred overnight. After cooling to room temperature, the reaction mixture was extracted with EtOAc (3 × 25 mL). The combined organic phases were washed with brine (20 mL) and dried over anhydrous Na2SO4. After filtration, the organic solvent was evaporated and the crude product was purified by automated flash chromatography using a gradient eluent from hexane to 20% EtOAc-hexane. The isoxazole product was then reacted with the corresponding 4-hydroxyquinoline using general procedure B for the preparation of compound 2h and 2i. (0236) [0159] 3-[[[8-trifluoromethoxy-2-trifluoromethyl-4-quinolinyl]oxy]methyl]-5- isoxazolecarboxylic Acid Ethyl Ester (2h): Yield 65%.1H NMR (CDCl3) 1.46 (3H, t, J = 7.2 Hz), 4.49 (2H, q, J = 7.2 Hz), 5.54 (2H, s), 7.17 (1H, s), 7.66 (1H, apparent t, J = 7.8 Hz), 7.74 (1H, d, J = 7.8 Hz) 8.20 (1H, d, J = 9.6 Hz).13C NMR (CDCl3) 14.1, 53.7, 62.3, 62.7, 98.1 (q, J = 2 Hz), 108.4, 120.6 (q, J = 259 Hz), 122.6 (q, J = 276 Hz), 123.0, 127.5, 128.1, 141.7 (q, J = 2 Hz), 149.8 (q, J = 35 Hz), 156.3, 159.4, 161.8, 163.5. HRMS (ESI): calcd. for C18H12F6N2O4 [M+H+] 434.0701, found 434.0704.
Reference： [1]Current Patent Assignee: DARTMOUTH COLLEGE - WO2017/136642, 2017, A1 Location in patent: Page/Page column 0148; 0158; 0159
  • 14
  • [ 82934-25-6 ]
  • [ 623-47-2 ]
  • [ 1141427-74-8 ]
YieldReaction ConditionsOperation in experiment
35% With sodium hypochlorite In tetrahydrofuran at 0 - 20℃; for 18h; 22.2 To a solution of (lE)-2-chloroacetaldehyde oxime (4.0 g, 42.8 mmol) in tetrahydrofuran (15 mL) was added ethyl prop-2 -ynoate (4.2 g, 42.8 mmol) and sodium hypochlorite (181.5 g, 243.8 mmol, 10% purity) at 0 °C. After stirred at 20 °C for 18 hours, the reaction mixture was diluted with ethyl acetate (200 mL) and brine (200 mL). The separated organic layer was dried over sodium sulphate and concentrated to dryness under reduced pressure. The residue was purified by column chromatography (silica gel, 100 - 200 mesh, 0 - 10% ethyl acetate in petroleum ether) to afford ethyl 3-(chloromethyl)isoxazole-5-carboxylate (2.8 g, 35%) as a white solid.
Reference： [1]Current Patent Assignee: TENAYA THERAPEUTICS INC - WO2021/127643, 2021, A1 Location in patent: Paragraph 00630-00631
  • 15
  • [ 1141427-74-8 ]
  • N-(3-chlorophenyl)-N-((5-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)isoxazol-3-yl)methyl)ethanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium carbonate / N,N-dimethyl-formamide / 16 h / 30 °C 2: hydrazine hydrate / ethanol / 2 h / 60 °C 3: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 4: Burgess Reagent / tetrahydrofuran / 2 h / 90 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: TENAYA THERAPEUTICS INC - WO2021/127643, 2021, A1
  • 16
  • [ 1141427-74-8 ]
  • N-(3-chlorophenyl)-N-[[5-[[(2,2-difluoroacetyl)amino]carbamoyl]isoxazol-3-yl]methyl]ethanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate / N,N-dimethyl-formamide / 16 h / 30 °C 2: hydrazine hydrate / ethanol / 2 h / 60 °C 3: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: TENAYA THERAPEUTICS INC - WO2021/127643, 2021, A1
  • 17
  • [ 1141427-74-8 ]
  • N-(3-chlorophenyl)-N-[[5-(hydrazinecarbonyl)isoxazol-3-yl]methyl]ethanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate / N,N-dimethyl-formamide / 16 h / 30 °C 2: hydrazine hydrate / ethanol / 2 h / 60 °C
Reference： [1]Current Patent Assignee: TENAYA THERAPEUTICS INC - WO2021/127643, 2021, A1
  • 18
  • [ 1141427-74-8 ]
  • 3-chloro-N-((5-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)isoxazol-3-yl)methyl)-N-methylaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium iodide; sodium carbonate / N,N-dimethyl-formamide / 2 h / 25 °C 2: hydrazine hydrate / ethanol / 2 h / 60 °C 3: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 °C 4: Burgess Reagent / tetrahydrofuran / 3 h / 90 °C / Microwave irradiation
Reference： [1]Current Patent Assignee: TENAYA THERAPEUTICS INC - WO2021/127643, 2021, A1
  • 19
  • [ 1141427-74-8 ]
  • 3-[(3-chloro-N-methylanilino)methyl]isoxazole-5-carbohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium iodide; sodium carbonate / N,N-dimethyl-formamide / 2 h / 25 °C 2: hydrazine hydrate / ethanol / 2 h / 60 °C
Reference： [1]Current Patent Assignee: TENAYA THERAPEUTICS INC - WO2021/127643, 2021, A1
  • 20
  • [ 1141427-74-8 ]
  • 3-[(3-chloro-N-methylanilino)methyl]-N'-(2,2-difluoroacetyl)isoxazole-5-carbohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium iodide; sodium carbonate / N,N-dimethyl-formamide / 2 h / 25 °C 2: hydrazine hydrate / ethanol / 2 h / 60 °C 3: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 °C
Reference： [1]Current Patent Assignee: TENAYA THERAPEUTICS INC - WO2021/127643, 2021, A1
  • 21
  • [ 1141427-74-8 ]
  • N-(3-chlorophenyl)ethanesulfonamide [ No CAS ]
  • ethyl 3-[(3-chloro-N-ethylsulfonylanilino)methyl]isoxazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With sodium carbonate In N,N-dimethyl-formamide at 30℃; for 16h; 22.3 To a solution of N-(3-chlorophenyl)ethanesulfonamide (461 mg, 2.10 mmol) in N,N-dimethylformamide (5 mL) was added ethyl 3-(chloromethyl)isoxazole-5-carboxylate (200 mg, 1.05 mmol) and sodium carbonate (334 mg, 3.15 mmol). After stirred at 30 °C for 16 hours, the mixture was diluted with ethyl acetate (50 mL) and washed with brine (50 mL x 2). The separated organic layer was dried over sodium sulphate and concentrated to dryness under reduced pressure. The residue was purified by column chromatography (silica gel, 100 - 200 mesh, 0 - 10% ethyl acetate in petroleum ether) to afford ethyl 3-[(3-chloro-N-ethylsulfonyl- anilino)methyl]isoxazole-5-carboxylate (370 mg, 95%) as a white solid.
Reference： [1]Current Patent Assignee: TENAYA THERAPEUTICS INC - WO2021/127643, 2021, A1 Location in patent: Paragraph 00632-00633
  • 22
  • [ 1141427-74-8 ]
  • [ 7006-52-2 ]
  • ethyl 3-[(3-chloro-N-methylanilino)methyl]isoxazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With sodium carbonate; potassium iodide In N,N-dimethyl-formamide at 25℃; for 2h; 24.1 To a solution of ethyl 3-(chloromethyl)isoxazole-5-carboxylate (300 mg, 1.58 mmol) in N,N-dimethylformamide (10 mL) was added 3-chloro-N-methyl-aniline (291 mg, 2.06 mmol), sodium carbonate (503 mg, 4.75 mmol) and potassium iodide (26 mg, 0.16 mmol). The reaction mixture was stirred at 25 °C for 2 hours and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 100 - 200 mesh, 0 - 15% ethyl acetate in petroleum ether) to afford ethyl 3-[(3-chloro-N-methyl- anilino)methyl]isoxazole-5-carboxylate (270 mg, 54%).
Reference： [1]Current Patent Assignee: TENAYA THERAPEUTICS INC - WO2021/127643, 2021, A1 Location in patent: Paragraph 00651-00652

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