[ CAS No. 55270-27-4 ]

Name: 55270-27-4|4-Bromoisoquinolin-1-amine|97%
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Quality Control of [ 55270-27-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 55270-27-4 ]

SDS Specification

Alternatived Products of [ 55270-27-4 ]

Product Details of [ 55270-27-4 ]

CAS No. :	55270-27-4	MDL No. :	MFCD05155261
Formula :	C₉H₇BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YWOLBIUYICZCLK-UHFFFAOYSA-N
M.W :	223.07	Pubchem ID :	311870
Synonyms :

Calculated chemistry of [ 55270-27-4 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	53.85
TPSA :	38.91 Å²

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) :	-5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.76
Log Po/w (XLOGP3) :	2.45
Log Po/w (WLOGP) :	2.59
Log Po/w (MLOGP) :	2.31
Log Po/w (SILICOS-IT) :	2.4
Consensus Log Po/w :	2.3

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.38
Solubility :	0.0923 mg/ml ; 0.000414 mol/l
Class :	Soluble
Log S (Ali) :	-2.91
Solubility :	0.274 mg/ml ; 0.00123 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.2
Solubility :	0.014 mg/ml ; 0.000063 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.65

Safety of [ 55270-27-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 55270-27-4 ]

* 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 [ 55270-27-4 ]
Downstream synthetic route of [ 55270-27-4 ]

[ 55270-27-4 ] Synthesis Path-Upstream 1~1

1
[ 1532-84-9 ]
[ 55270-27-4 ]

Reference： [1] Journal of Organic Chemistry, 2001, vol. 66, # 4, p. 1310 - 1315

[ 55270-27-4 ] Synthesis Path-Downstream 1~11

3
[ 1532-84-9 ]
[ 55270-27-4 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 1310 - 1315

4
[ 75-11-6 ]
[ 55270-27-4 ]
5,11-dibromo-8H-diisoquinolino[1,2-a:2',1'-d][1,3,5]triazin-7-ium iodide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 1310 - 1315

5
[ 55270-27-4 ]
4-bromo-2-(4-bromo-1-imino-3-1H-isoquinolin-2-ylmethyl)-2H-isoquinolin-1-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 1310 - 1315

6
[ 1257295-19-4 ]
[ 55270-27-4 ]
[ 1257296-13-1 ]

Yield	Reaction Conditions	Operation in experiment
	tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 140℃;Microwave irradiation; Inert atmosphere;	To intermediate 37 in a microwave vial is added 1.2 equivalents of an arylbromide, 1 equivalent of copper (I) iodide or copper thiophene-carboxylate, and 1,4-dioxaneas solvent. The reaction mixture is degassed under nitrogen for 5 minutes prior to addition of0.12 equivalents oftetrakis(triphenylphosphine)palladium(0). The reaction is heated in aCEM or Biotage microwave for 20-30 minutes at 140C. The crude reaction mixture isfiltered and periodically passed through a Biotage Isolute scx-2 basic spe cartridge beforebeing purified via normal or reverse phase chromatography to afford pure product 38.Substituents R2 and R3 may be R2 and R3 as defined, or protected forms or precursorsthereof.; 2-(l-((9-Methyl-6-morpholino-2-(tributylstannyl)-9H-purin-8- yl)methyl)piperidin-4-yl)propan-2-ol (0.1 g) was reacted with 4-bromoisoquinolin-l -amine via General Procedure G to afford 115 following reverse phase purification. MS (Ql) 517.3 (M)+,'H NMR (400 MHz, DMSO) delta 9.01 (d, IH), 8.56 (s, IH), 8.25 (d, IH), 7.67 (t, IH), 7.49 (t, IH), 7.07 (s, 2H), 4.23 (s, 4H), 4.02 (s, IH), 3.87 - 3.66 (m, 10H), 2.89 (d, 3H), 1.99 (t, 2H), 1.66 (d, 2H), 1.35 - 1.10 (m, 3H), 1.02 (s, 6H).

Reference： [1]Patent: WO2010/138589,2010,A1 .Location in patent: Page/Page column 250; 396

7
C₃₆H₅₅FN₂O₁₂ [ No CAS ]
[ 55270-27-4 ]
C₄₅H₆₁FN₄O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In acetonitrile; at 80℃; for 4h;Sonication; Inert atmosphere;	0.80 g (1.17 mmol) of compound 6 was dissolved in 20 mL of acetonitrile (degassed by ultrasonic)(Triphenylphosphine) palladium dichloride (41 mg, 0.058 mmol)22 mg (0.12 mmol) of cuprous iodide,Triethylamine 0.24 mL (1.75 mmol)And 0.91 g (4.09 mmol) of <strong>[55270-27-4]1-amino-4-bromoisoquinoline</strong>.The reaction system was replaced with argon for 5 times under argon,And stirred at 80 C for 4 h.After completion of the TLC monitoring reaction, distilled water (20 mL) was added to terminate the reaction,Extracted with ethyl acetate (40 mL)The upper organic phase was washed with saturated brine (20 mL)Steamed and concentrated to dry the solid.Column chromatography (100-200 mesh silica gel column,The mobile phase was V (dichloromethane): V (ethanol): V (aqueous ammonia) = 10: 0.2: 0.1)The 2'-O-acetyl-product 12 was isolated.2'-O-acetyl-product 12 was dissolved in 20 mL of methanol, refluxed at 65 C for 3 h,TLC monitoring reaction is complete, concentrated under reduced pressure,To give a dry product.Column chromatography (200-300 mesh silica gel column, mobile phase V (dichloromethane):V (ethanol): V (ammonia) = 10: 0.2:0.1) to give pure product 12 (29 mg, 0.035 mmol)Product 12 is 2-fluoro-3-O-decapramide-3-carbonyl-6-O-methylerythromycinA 9-O- [3- [4 '- (1'-amino) isoquinolinyl] -2-propynyl] oxime 11,12-cyclic carbonate,The yield is3.0%.

Reference： [1]Patent: CN106916194,2017,A .Location in patent: Paragraph 0149; 0150

8
2-chloro-2-(ethylthio)-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethan-1-one [ No CAS ]
[ 55270-27-4 ]
6-bromo-3-(ethylsulfonyl)-2-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]imidazo[2,1-a]isoquinoline [ No CAS ]

Reference： [1]Patent: JP2018/90578,2018,A

9
2-chloro-2-(ethylthio)-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethan-1-one [ No CAS ]
[ 55270-27-4 ]
6-bromo-3-(ethylthio)-2-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]imidazo[2,1-a]isoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
198 mg		2-chloro-2- (ethylthio) -1-[3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethan-1-one200 mg of acetonitrile and 3 ml of acetonitrile,At room temperature, 110 mg of <strong>[55270-27-4]4-bromoisoquinolin-1-amine</strong> was added.The mixture was stirred under heating reflux for 30 minutes.To the reaction mixture was added 50 mg of sodium hydrogencarbonate at room temperature.The reaction mixture was stirred under heating reflux for 4 hours.After completion of the reaction, 3 ml of water and 1 ml of 12 mol / L hydrochloric acid were added to the reaction mixture at room temperature.After filtering the precipitated solid, the obtained solid was washed with water,To obtain 198 mg of the objective compound as an orange solid.

Reference： [1]Patent: JP2018/90578,2018,A .Location in patent: Paragraph 0257

10
[ 55270-27-4 ]
[ 110-13-4 ]
ethyl 1-(2-chloro-4-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42.7%	With toluene-4-sulfonic acid; In toluene; for 36h;Reflux;	A solution of <strong>[55270-27-4]4-bromoisoquinolin-1-amine</strong> (5.5 g, 24.656 mmol), hexane-2,5-dione (3.377 g, 29.59 mmol) and p-TSA (93.8 mg, 0.49 mmol) in toluene (50 mL) was heated to reflux for 36 h. The mixture was concentrated under reduced pressure. The crude product was purified by column chromatography over silica gel (petroleum ether/ethyl acetate from 100/0 to 0/100). The desired fractions were collected and the solvent was concentrated under reduced pressure to afford the title product (3.3 g, 42.7% yield) as a white solid. LCMS (ESI) m/z M+1: 302.9.

Reference： [1]Patent: US2018/170909,2018,A1 .Location in patent: Paragraph 1680; 1681

11
2'-O-acetyl-2-F-3-O-descladinosyl-3-keto-6-O-methylerythromycin A 9-O-propargyl oxime 11,12-cyclic carbonate [ No CAS ]
[ 55270-27-4 ]
2-fluoro-3-O-descladinosyl-3-oxo-6-O-methylerythromycin A-9-O-[3-(1'-aminoisoquinol-4'-yl)-2-propargyl]oxime-11,12-cyclic carbonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.01%		General procedure: To a solution of CuI (0.1 eq), Pd(PPh3)2Cl2 (0.05 eq) and compound7 (1 eq) in MeCN (5 mL) were added ArBr (Ar a, b, c, e, f, g,h, k, l) or ArI (Ar q, r, s, t) (3 eq) and trimethylamine (1.5 eq). Thereaction mixture was flushed with argon and sealed in a pressuretube. The reaction mixture was stirred at 80 C for 3-4 h. The reactionmixture was extracted with EtOAc, washed with water andbrine and concentrated in vacuo. The product was dissolved inMeOH (15 mL) at 60 C for 1 h. The organic solvent was removed invacuum. The crude mixture was purified by column chromatographyon silica gel to give 8a, 8b, 8c, 8e, 8f, 8g, 8h, 8k, 8l, 8q, 8r, 8s,8t.To a solution of ArI (Ar = n, p) (3 eq) in MeCN (5 mL) was addedtrimethylamine (5 mL). The mixture was stirred at room temperaturefor 1 h, after which time CuI (0.1 eq), Pd(PPh3)2Cl2 (0.05 eq)and compound 7 (1 eq) were added. The reaction mixture wasflushed with argon and sealed in a pressure tube. The reactionmixture was stirred at 50 C for 24 h. The reaction mixture wasextracted with EtOAc, washed with water and brine and concentratedin vacuum. The product was then dissolved in MeOH (15 mL)at 60 C for 1 h. The organic solvent was removed in vacuo. Thecrude mixturewas purified by column chromatography on silica gelto give 8n and 8p.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 169,p. 1 - 20

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Code	Phrase
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P321
P322
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P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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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.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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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
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H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
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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. 55270-27-4 ]

Quality Control of [ 55270-27-4 ]

Related Doc. of [ 55270-27-4 ]

Product Details of [ 55270-27-4 ]

Calculated chemistry of [ 55270-27-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 55270-27-4 ]

Application In Synthesis of [ 55270-27-4 ]

[ 55270-27-4 ] Synthesis Path-Upstream 1~1

[ 55270-27-4 ] Synthesis Path-Downstream 1~11

Related Functional Groups of [ 55270-27-4 ]

Bromides

Amines

Related Parent Nucleus of [ 55270-27-4 ]

Isoquinolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 55270-27-4 ]

Related Parent Nucleus of
[ 55270-27-4 ]