433926-46-6|3-Chloro-5-(trifluoromethoxy)benzoic acid| Ambeed

CAS No. :	433926-46-6
Formula :	C₈H₄ClF₃O₃
M.W :	240.56
SMILES Code :	O=C(O)C1=CC(OC(F)(F)F)=CC(Cl)=C1
MDL No. :	MFCD06660306
InChI Key :	KVXQRRFQLRUCKN-UHFFFAOYSA-N
Pubchem ID :	17750735

Safety of [ 433926-46-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340-P405-P501

Application In Synthesis of [ 433926-46-6 ]

* 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 [ 433926-46-6 ]

[ 433926-46-6 ] Synthesis Path-Downstream 1~6

1
[ 633336-69-3 ]
[ 433926-46-6 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 2-amino-3-chloro-5-trifluoromethoxybenzoic acid (60.5 g, assume 0.22 mol; see step (iii) above) in 1,4-dioxane (1000 mL) was added 6N HCl (750 mL). Some organics oiled out of solution. The dioxane solution was cooled to less than 0 C. (ice-MeOH bath). A solution of sodium nitrite (18.2 g, 0.26 mol) in H2O (250 mL) was added over 15 minutes via an addition funnel. The resulting solution was stirred for 45 min. Hypophosphorous acid (221.5 mL of 50 wt % in H2O, 291.2 g, 2.20 mol) was added slowly via an addition funnel. The solution was stirred at 0 C. for 1.5 hours, then warmed to room temperature (gas evolution observed) and stirred for 18 hours. The crude solution was transferred to a separating funnel and extracted with Et2O (4). The combined organics were extracted with aqueous NaHCO3 (3). The basic aqueous layer was cautiously acidified with 6N HCl and extracted with CH2Cl2 (3*). The CH2Cl2 extracts were dried (Na2SO4), filtered and concentrated in vacuo to give the crude sub-title compound (26.5 g, 46% from 3-trifluoromethoxybenzoic acid) as a solid that was used in the next step without further purification. 1H NMR (300 MHz, CD3OD): δ7.98 (s, 1H), 7.83 (s, 1H), 7.58 (s, 1H)
		To a solution of 2-amino-3-chloro-5-trifluoromethoxybenzoic acid (60.5 g, assume 0.22 mol; see step (iii) above) in 1,4-dioxane (1000 mL) was added 6N HCI (750 mL). Some organics oiled out of solution. The dioxane solution was cooled to less than [0C] (ice- MeOH bath). A solution of sodium nitrite (18.2 g, 0.26 mol) in H20 (250 mL) was added over 15 minutes via an addition funnel. The resulting solution was stirred for 45 min. Hypophosphorous acid (221.5 mL of 50 wt% in HDO, 291.2 g, 2.20 mol) was added slowly via an addition funnel. The solution was stirred at [0C] for 1.5 hours, then warmed to room temperature (gas evolution observed) and stirred for 18 hours. The crude solution was transferred to a separating funnel and extracted with [ET20] (4x). The combined organics were extracted with aqueous [NAHC03] (3x). The basic aqueous layer was cautiously acidified with 6N HCI and extracted with [CH2C12] (3x). The [CH2CI2] extracts were dried [(NA2SO4),] filtered and concentrated in vacuo to give the crude sub-title compound (26.5 g, 46% from 3-trifluoromethoxybenzoic acid) as a solid that was used in the next step without further purification. 'H NMR (300 MHz, CD30D) : A 7.98 (s, 1H), 7.83 (s, 1H), 7.58 (s, 1H)

References: [1]Patent: US2004/19033,2004,A1 .Location in patent: Page/Page column 18-19.
[2]Patent: WO2003/101956,2003,A1 .Location in patent: Page 48.

2
[ 433926-46-6 ]
[ 433926-47-7 ]

Yield	Reaction Conditions	Operation in experiment
100%		To a solution of 3-chloro-5-trifluoromethoxybenzoic acid (22.5 g, 93.5 mmol; see step (iv) above) in anhydrous THF (1200 mL) under a N2 atmosphere at room temperature was added a solution of BH3.THF complex (140 mL of 1M in THF; 140.3 mmol). The solution was refluxed for 2 h, cooled to room temperature and stirred for 18 hours, quenched cautiously with H2O and concentrated in vacuo to remove most of the THF. The residue was diluted with EtOAc and the organics were washed with brine (3*), dried (Na2SO4), filtered and concentrated in vacuo to give the crude sub-title compound (21.2 g, 100%) as an oil that was used without further purification. 1H NMR (300 MHz, CDCl3): δ7.33 (s, 1H), 7.17 (s, 1H), 7.14 (s, 1H), 4.72 (s, 2H), 2.05 (br s, 1H)
100%	With borane-THF; In tetrahydrofuran; at 20℃; for 20h;Heating / reflux;	To a solution of 3-chloro-5-trifluoromethoxybenzoic acid (22.5 g, 93.5 mmol; see step (iv) above) in anhydrous THF (1200 mL) under a N2 atmosphere at room temperature was added a solution of [BH3THF] complex (140 mL of 1M in THF; 140.3 mmol). The solution was refluxed for 2 h, cooled to room temperature and stirred for 18 hours, quenched cautiously with [HZO] and concentrated in vacuo to remove most of the THF. The residue was diluted with EtOAc and the organics were washed with brine (3x), dried [(NA2SO4),] filtered and concentrated in vacuo to give the crude sub-title compound (21.2 g, [100%)] as an oil that was used without further purification. 'H NMR (300 MHz, [CDCI3)] : A 7.33 (s, 1H), 7.17 (s, 1H), 7.14 (s, 1H), 4.72 (s, 2H), 2.05 [(BRS, 1H)]

References: [1]Patent: US2004/19033,2004,A1 .Location in patent: Page/Page column 19.
[2]Patent: WO2003/101956,2003,A1 .Location in patent: Page 48; 49.

3
[ 433926-46-6 ]
[ 1174512-15-2 ]
[ 1261173-50-5 ]

Yield	Reaction Conditions	Operation in experiment
		Example 1.17: Preparation of 2-(9-Chloro-7-(5-(3-chloro-5-(trifluoromethoxy) phenyl)- l,2,4-oxadiazol-3-yl)-2,3-dihydro-lH-pyrrolo[l,2-a]indol-l-yl)acetic Acid (Compound 16).Step A: Preparation of tø/t-Butyl 2-(7-(5-(3-Chloro-5-(trifluoromethoxy)phenyl)-1 ,2,4-oxadiazol-3-yl)-2,3-dihydro-l/-r-pyrrolo [1 ,2-a] indol-l-yl)acetate.To a stirred solution of <strong>[433926-46-6]3-chloro-5-(trifluoromethoxy)benzoic acid</strong> (51 mg, 0.213 mmol) and HATU (105 mg, 0.276 mmol) in DMF (1 mL) was added DIEA (74.0 μL, 0.425 mmol). After 15 min, tert-butyl 2-(7-(N-hydroxycarbamimidoyl)-2,3-dihydro-lH-pyrrolo[l,2-a]indol-l- yl)acetate (70 mg, 0.213 mmol) was added. The reaction mixture was stirred at room temperature for 30 min, then heated at 70 0C for 1 h, and cooled down. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give the title compound as a white solid (80 mg). LCMS m/z = 534.4 [M+Η]+; 1H ΝMR (400 MHz, CDCl3) 1.51 (s, 9H), 2.28-2.38 (m, IH), 2.55 (dd, J = 15.8 and 8.2 Hz, IH), 2.78 (dd, J= 15.8 and 6.6 Hz, IH), 2.88-2.96 (m, IH), 3.72-3.80 (m, IH), 4.02-4.11 (m, IH), 4.15-4.23 (m, IH), 6.28 (s, IH), 7.32 (d, J= 8.5 Hz, IH), 7.45 (s, IH), 7.93 (dd, J= 8.5 and 1.5 Hz, IH), 7.99 (s, IH), 8.17 (t, 7= 1.3 Hz, IH), 8.39 (d, 7= 1.3 Hz, IH).

References: [1]Patent: WO2011/5290,2011,A1 .Location in patent: Page/Page column 65.

4
[ 433926-46-6 ]
6-{5-[(1S)-1-aminoethyl]-1H-1,2,4-triazol-1-yl}nicotinonitrile hydrochloride [ No CAS ]
[ 7087-68-5 ]
3-chloro-N-{(1S)-1-[1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoromethoxy)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
198 mg		A mixture of 211 mg (0.87 mmol) <strong>[433926-46-6]3-chloro-5-(trifluoromethoxy)benzoic acid</strong>, 605 mg (1.59 mmol) 1- [Bis(dimethylamino)methylene]-lH-l,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), 0.31 mL (2.4 mmol) A-Ethyldiisopropylamine and 3 mL acetonitrile was stirred for 60 min at room temperature. 200 mg of the residue containing 6- {5-[(lS)-l-aminoethyl]-lH-l,2,4-triazol-l - yl \| nicotinonitrilc hydrochloride from the previous step and 1 ml acetonitrile were added and the mixture stirred for 2 d at room temperature. The mixture was then diluted with acetonitrile and adsorbed onto reversed phase silica gel. Purification by reversed phase chromatography (0 / acetonitrile) provided 198 mg 3-chloro-N- {(l S)-l-[l-(5-cyanopyridin-2-yl)-lH-l,2,4-triazol-5-yl]ethyl} -5- (0659) (trifluoromethoxy)benzamide. (0660) NMR (DMSO-de, 400 MHz): d= 9.3719 (3.1); 9.3545 (3.2); 9.0610 (5.4); 9.0593 (6.0); 9.0556 (5.9); 9.0537 (5.7); 8.5843 (5.2); 8.5788 (4.9); 8.5629 (5.5); 8.5573 (5.5); 8.3160 (1.0); 8.2462 (16.0); 8.0840 (6.3); 8.0822 (6.4); 8.0626 (5.9); 8.0607 (6.0); 7.9588 (4.8); 7.9546 (7.4); 7.9507 (5.1); 7.7824 (4.4); 7.7325 (4.5); 7.7299 (4.8); 7.7272 (4.0); 6.1038 (0.5); 6.0863 (2.4); 6.0689 (3.8); 6.0516 (2.4); 6.0340 (0.5); 3.3243 (352.4); 2.6802 (1.1); 2.6757 (2.4); 2.6710 (3.4); 2.6665 (2.4); 2.6619 (1.1); 2.5246 (10.1); 2.5199 (14.8); 2.5112 (196.8); 2.5067 (404.5); 2.5021 (530.9); 2.4975 (372.2); 2.4929 (172.6); 2.3380 (1.1); 2.3335 (2.4); 2.3289 (3.3); 2.3243 (2.4); 2.3197 (1.1); 2.0745 (0.4); 1.6382 (14.6); 1.6208 (14.6); 0.1459 (2.5); 0.0080 (20.9); -0.0001 (646.4); -0.0086 (19.8); -0.1496 (2.5). (0661) ESI mass [m/z]: 437.2 [M+H]+

References: [1]Patent: WO2019/206799,2019,A1 .Location in patent: Page/Page column 126.

5
[ 433926-46-6 ]
1-(5-chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine [ No CAS ]
3-chloro-N-[1-(5-chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethoxy)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
122 mg	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃;	To 150.0 mg (0.66 mmol) l-(5-chloro-2-pyrimidin-2-yl-l,2,4-triazol-3-yl)ethanamine, 164.0 mg (0.66 mmol) 3-chloro-5-(trifluoromethoxy)-benzoic acid, 120 mg (0.92 mmol) DIPEA in DMF (3 mL), 310.0 mg (0.81 mmol) HATU were added, and the reaction mixture was stirred at room temperature over night. The reaction mixture was concentrated under reduced pressure and the solid residue was treated with dichloromethane and then extracted with a saturated aqueous NaHCCF solution and water. The organic phase was separated, dried over NaiSCF and the solvent was evaporated under reduced pressure. The remaining solid residue was purified by HPLC with a water/acetonitrile neutral gradient to obtain 122.0 mg (purity: 98.8 %; yield: 41 %) of the racemic title compound. Formula: Ci8HnBrN602 Molecular weight: 447.20 g/mol HPFC-MS neutral (ESI positive) [m/z]: 447.1 [M+H]+

References: [1]Patent: WO2021/69569,2021,A1 .Location in patent: Page/Page column 75; 78.

6
[ 433926-46-6 ]
1-[2-(5-chloro-2-pyridyl)-5-(6-chloro-3-pyridyl)-1,2,4-triazol-3-yl]ethanamine [ No CAS ]
(S)-3-chloro-N-[1-[2-(5-chloro-2-pyridyl)-5-(6-chloro-3-pyridyl)-1,2,4-triazol-3-yl]ethyl]-5-(trifluoromethoxy)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃;	To 222.9 mg (0.66 mmol) 1-[2-(5-chloro-2-pyridyl)-5-(6-chloro-3-pyridyl)-1,2,4-triazol-3-yl]ethanamine (INT-006), 235.6 mg (0.95 mmol) 3-chloro-5-(trifluoromethoxy)-benzoic acid, 614.0 mg (4.75 mmol) DIPEA in DMF (6.5 mL), 433.5 mg (1.14 mmol) HATU was added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered, concentrated and the residue was purified by HPLC with a MeCN/water gradient (acid) to afford 103.6 mg (purity: 100 %; yield: 16 %) of the title compound. The enantiomeric excess of the (S)-enantiomer has been determined via screen OD_RH (acid): ee-value = 90%; Rt = 16.54 min. Formula: C22H14Cl3F3N6O2 Molecular weight: 557.75 g/mol HPLC-MS acid (ESI positive): 557.1 [M+H]+

References: [1]Patent: WO2021/69567,2021,A1 .Location in patent: Page/Page column 194-195.

Historical Records

Technical Information

• Alkyl Halide Occurrence • Arndt-Eistert Homologation • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hunsdiecker-Borodin Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Nomenclature of Ethers • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Preparation of Ethers • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Reactions of Ethers • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Ugi Reaction

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H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 433926-46-6

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