[ CAS No. 1211577-99-9 ] {[proInfo.proName]}

Name: 1211577-99-9|6-(Difluoromethoxy)nicotinaldehyde|98%
Brand: Ambeed
SKU: A245323
Price: 15.0 USD
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3d Animation Molecule Structure of 1211577-99-9

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Quality Control of [ 1211577-99-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1211577-99-9 ]

SDS Specification

Alternatived Products of [ 1211577-99-9 ]

Product Details of [ 1211577-99-9 ]

CAS No. :	1211577-99-9	MDL No. :	MFCD18261899
Formula :	C₇H₅F₂NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NRGBKYVUEUMGTE-UHFFFAOYSA-N
M.W :	173.12	Pubchem ID :	21698508
Synonyms :

Calculated chemistry of [ 1211577-99-9 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	3
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	36.22
TPSA :	39.19 Å²

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) :	-6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.41
Log Po/w (XLOGP3) :	1.57
Log Po/w (WLOGP) :	2.34
Log Po/w (MLOGP) :	0.25
Log Po/w (SILICOS-IT) :	1.9
Consensus Log Po/w :	1.5

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.07
Solubility :	1.46 mg/ml ; 0.00843 mol/l
Class :	Soluble
Log S (Ali) :	-2.0
Solubility :	1.72 mg/ml ; 0.00992 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.32
Solubility :	0.834 mg/ml ; 0.00482 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.73

Safety of [ 1211577-99-9 ]

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 [ 1211577-99-9 ]

* 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.

Downstream synthetic route of [ 1211577-99-9 ]

[ 1211577-99-9 ] Synthesis Path-Downstream 1~9

1
[ 899452-26-7 ]
[ 68-12-2 ]
[ 1211577-99-9 ]

Yield	Reaction Conditions	Operation in experiment
30%	Stage #1: 5-bromo-2-(difluoromethoxy)pyridine With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.416667h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide at -78℃; for 0.333333h;	3 6-(difluoromethoxy)nicotinaldehyde To 5-bromo-2-(difluoromethoxy)pyridine (448 mg, 2.00 mmol, 1.00 equiv; Ando, M. eta., Org. Lett. 2006, 8:3805-3808) in THF (10 mL) at -78 °C and under an atmosphere of N2, was added t-BuLi (1.7 M in pentane, 2.35 mL, 4.00 mmol, 2.00 equiv) dropwise over 5 mm. After stirring for 20 mm at -78 °C, DMF (0.54 mL, 7.0 mmol, 3.5 equiv) was added to the reaction mixture. After stirring for 20 mm at -78 °C, iN HC1 aq (10 mL) was added and the resulting mixture was warmed to 23 °C. The phases were separated and the aqueous phase was extracted with EtOAc (3 x 5 mL). The combined organic phases were washed with brine (10 mL), dried (Mg504), and filtered. The filtrate was concentrated in vacuo and the resulting residue was purified by silica gel column chromatography eluting with hexanes/EtOAc to afford 105 mg of the title compound (30% yield).NMR Spectroscopy: ‘H NMR (300 MHz, CDC13): ö 10.05 (s, 1H), 8.69 (d, J 2.1 Hz, 1H), 8.24 (dd, J 8.4 Hz, 2.4 Hz, 1H), 7.56 (t, J 72.3 Hz, 1H), 7.04 (d, J 8.4 Hz, 1H). ‘9F NMR (282 MHz, CDC13): ö -89.8 (d, J 72.3 Hz, 2F).

Reference： [1]Current Patent Assignee: OCUTERRA THERAPEUTICS INC - WO2016/134223, 2016, A2 Location in patent: Page/Page column 67

2
[ 1211577-99-9 ]
[ 1621615-00-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 1 h / 23 - 50 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: OCUTERRA THERAPEUTICS INC - WO2016/134223, 2016, A2

3
[ 1211577-99-9 ]
[ 227752-03-6 ]
[ 1621614-99-0 ]

Yield	Reaction Conditions	Operation in experiment
71%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In acetonitrile at 23 - 50℃; for 1h; Inert atmosphere;	3 (F)- 1-(6-(difluoromethoxy)pyridin-3-yl)-7-(5,6,7,8-tetrahydro- 1,8-naphthyridin- 2-yl)hept-1-en-3-one To dimethyl (2-oxo-6-(5,6,7, 8-tetrahydro- 1 ,8-naphthyridin-2-yl)hexyl)phosphonate (1.57 g, 4.62 mmol, 1.00 equiv) in MeCN (11 mL) at 23 °C and under an atmosphere of N2, was added 6-(difluoromethoxy)nicotinaldehyde (800 mg, 4.62 mmol, 1.00 equiv), LiC1 (196 mg, 4.62 mmol, 1.00 equiv) and DBU (0.725 mL, 4.85 mmol, 1.05 equiv). After stirring for 1 hr at 50 °C, the reaction mixture was cooled to 23 °C and then filtered through a pad of CELITE. The filtrate was concentrated in vacuo and the resulting residue was purified by silica gel column chromatography eluting with CH2C12/MeOH to afford 1.27 g of the title compound (71% yield).NMR Spectroscopy: ‘H NMR (300 MHz, CDC13): ö 8.32 (d, J= 2.4 Hz, 1H), 7.92 (dd, J8.4 Hz, 2.4 Hz, 1H), 7.49 (t, J= 72.3 Hz, 1H), 7.47 (d, J 16.2 Hz, 1H), 7.06 (d, J 7.2 Hz, 1H), 6.93 (d, J= 8.7 Hz, 1H), 6.70 (d, J= 16.2 Hz, 1H), 6.35 (d, J= 7.2 Hz, 1H), 4.89 (br s, 1H), 3.42-3.36 (m, 2H), 2.76-2.64 (m, 4H), 2.62-2.56 (m, 2H), 1.94-1.85 (m, 2H), 1.80-1.66 (m, 4H). ‘9F NMR (282 MHz, CDC13): ö -89.2 (d, J 72.3 Hz, 2F).

Reference： [1]Current Patent Assignee: OCUTERRA THERAPEUTICS INC - WO2016/134223, 2016, A2 Location in patent: Page/Page column 67; 68

4
[ 13466-38-1 ]
[ 1211577-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: acetonitrile / 48 h / 70 °C 2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.42 h / -78 °C / Inert atmosphere 2.2: 0.33 h / -78 °C

Reference： [1]Current Patent Assignee: OCUTERRA THERAPEUTICS INC - WO2016/134223, 2016, A2

5
[ 1211577-99-9 ]
[ 2222756-86-5 ]
[ 2222754-59-6 ]

Yield	Reaction Conditions	Operation in experiment
44%	With sodium tris(acetoxy)borohydride; triethylamine In N,N-dimethyl acetamide at 20℃;	500 1 -((3 -chloro-4-(6-(6-((6-methoxypyridin-3 -yl)methyl)-3 ,6-diazabicyclo[3. 1.1 ]heptan3 -yl)pyridin-3 -yl)pyrazolo[ 1,5 -a]pyridin-6-yl)oxy)-2-methylpropan-2-ol General procedure: A solution of 1 -((4-(6-(3 ,6-diazabicyclo[3.1. 1 ]heptan-3-yl)pyridin-3 -yl)-3 -chloropyrazolo[ 1,5 -a]pyridin-6-yl)oxy)-2-methylpropan-2-ol 2,2,2-trifluoroacetate(Intermediate P92; 50 mg, 0.098 mmol) in DMA (750 tL) was treated with TEA (150 tL, 0.098 mmol), 6-methoxynicotinaldehyde (40 mg, 0.29 mmol) and NaBH(AcO)3 (62.1 mg, 0.293 mmol). After stirring for 3 h at ambient temperature, the reaction mixture was quenched with water and extracted with DCM (3x). The combined organic extracts were dried over anhydrous Na2SO4(), filtered and concentrated in vacuo. The crude residue was purified by silica chromatography (using 0-20% MeOH (2% NH4OH)/DCM with as the gradient eluent) to afford the title compound (49.5 mg, 95% yield). MS (apci) m/z = 535.2 (M+H).

Reference： [1]Current Patent Assignee: PFIZER INC; ELI LILLY & CO - WO2018/71447, 2018, A1 Location in patent: Paragraph 002212; 002213; 002214; 002218; 002219; 002220

6
[ 1211577-99-9 ]
[ 373-88-6 ]
[ 2724247-96-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In acetonitrile at 0 - 20℃; for 48h; Inert atmosphere;	1 (E)-1-(6-(difluoromethoxy)pyridin-3-yl)-N-(2,2,2-trifluoroethyl)methanimine (Intermediate of Formula (II-7)) To a stirred solution of 6-(difluoromethoxy)nicotinaldehyde (IIa-7) (500 mg, 2.89 mmol) in acetonitrile (20 ml) at 0°C under nitrogen was added 2,2,2-trifluoroethanamine hydrochloride (1.5 g, 11.5 mmol), followed by triethylamine (2.4 ml, 17.3 mmol) and the reaction mixture stirred at rt for 48 h. The reaction was concentrated in vacuo to give the title compound (II-7) as a crude oil which was used in the next step without further purification.

Reference： [1]Current Patent Assignee: UNIVERSITY OF KENTUCKY; MMV MEDICINES FOR MALARIA VENTURE PPP - EP3892332, 2021, A1 Location in patent: Paragraph 0193-0194

7
[ 1211577-99-9 ]
[ 2724247-73-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylamine / acetonitrile / 48 h / 0 - 20 °C / Inert atmosphere 2.1: dichloromethane / 16 h / 20 °C / Inert atmosphere 3.1: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 16 h / 50 °C / Inert atmosphere 3.2: 4 h / Inert atmosphere

Reference： [1]Current Patent Assignee: UNIVERSITY OF KENTUCKY; MMV MEDICINES FOR MALARIA VENTURE PPP - EP3892332, 2021, A1

8
[ 1211577-99-9 ]
[ 2724247-97-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / 48 h / 0 - 20 °C / Inert atmosphere 2: dichloromethane / 16 h / 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: UNIVERSITY OF KENTUCKY; MMV MEDICINES FOR MALARIA VENTURE PPP - EP3892332, 2021, A1

9
[ 2831289-33-7 ]
[ 106984-91-2 ]
[ 1211577-99-9 ]

Yield	Reaction Conditions	Operation in experiment
64%	In acetonitrile at 85℃; for 72h; Inert atmosphere;	1 Synthesis of (3S,4S)-N-(3-cyano-4-fluorophenyl)-3-(6-(difluoromethoxy)pyridin-3-yl)-1-oxo-2-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroisoguinoline-4-carboxamide (7) 6-(Difluoromethoxy)nicotinaldehyde (intermediate of Formula (Intermediate of Formula (IIa-7)) To a stirred solution of 6-hydroxynicotinaldehyde (iv) (2.0 g, 16.2 mmol) in acetonitrile (60 mL) at rt under nitrogen was added sodium chlorodifluoroacetate (3.7 g, 24.4 mmol). The reaction mixture was heated at 85°C for 72 h then the reaction was quenched by the addition of distilled water (10 mL) and the mixture extracted with ethylacetate (3 x 20 mL), the combined extracts dried (Na2SO4), filtered and concentrated in vacuo and the resulting white gum subjected to column chromatography (SiO2, 1:5 ethyl acetate : hexane) to give the title compound (IIa-7) (1.8 g, 10.4 mmol, 64%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.06 (s, 1H), 8.84 (s, 1H), 8.34 (dd, J = 8.52, Hz, 2.16 Hz, 1H), 8.01-7.65 (m, 1H), 7.28 (d, J = 8.56 Hz, 1H).

Reference： [1]Current Patent Assignee: UNIVERSITY OF KENTUCKY; MMV MEDICINES FOR MALARIA VENTURE PPP - EP3892332, 2021, A1 Location in patent: Paragraph 0191-0192

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Ghs Precautionary Statements

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Code	Phrase
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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P230	Keep wetted
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P240	Ground/bond container and receiving equipment.
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P322
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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
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

[ CAS No. 1211577-99-9 ] {[proInfo.proName]}

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[ 1211577-99-9 ] Synthesis Path-Downstream 1~9

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Fluorinated Building Blocks

Aldehydes

Ethers

Difluoromethyls

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Pyridines

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[ 1211577-99-9 ]

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[ 1211577-99-9 ]