[ CAS No. 380381-36-2 ] {[proInfo.proName]}

Name: 380381-36-2|5-Iodo-N,N-dimethylpyridin-2-amine|97%
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Quality Control of [ 380381-36-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 380381-36-2 ]

SDS Specification

Alternatived Products of [ 380381-36-2 ]

Product Details of [ 380381-36-2 ]

CAS No. :	380381-36-2	MDL No. :	MFCD18207670
Formula :	C₇H₉IN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KWBFQSXLPGXDAP-UHFFFAOYSA-N
M.W :	248.06	Pubchem ID :	23438579
Synonyms :

Calculated chemistry of [ 380381-36-2 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	51.16
TPSA :	16.13 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) :	-6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.01
Log Po/w (XLOGP3) :	1.96
Log Po/w (WLOGP) :	1.75
Log Po/w (MLOGP) :	1.81
Log Po/w (SILICOS-IT) :	1.85
Consensus Log Po/w :	1.88

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.99
Solubility :	0.253 mg/ml ; 0.00102 mol/l
Class :	Soluble
Log S (Ali) :	-1.92
Solubility :	2.96 mg/ml ; 0.0119 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.09
Solubility :	0.201 mg/ml ; 0.000811 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.43

Safety of [ 380381-36-2 ]

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 [ 380381-36-2 ]

* 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 [ 380381-36-2 ]
Downstream synthetic route of [ 380381-36-2 ]

[ 380381-36-2 ] Synthesis Path-Upstream 1~4

1
[ 280116-78-1 ]
[ 74-88-4 ]
[ 380381-36-2 ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium carbonate In ISOPROPYLAMIDE at 90℃; for 24 h;	The obtained 2-(N-monomethylamino)-5-iodopyridine (99, 1.00 g, 4.27 mmol), potassium carbonate (2.95 g, 21.36 mmol) and iodomethane (145 mg, 8.546 mmol) were dissolved in dimethylacetamide (30 mL), and the reaction mixture was heated at 90° C. for 24 hours, followed by adding water. Organic compounds were extracted with ethyl acetate and evaporated after a treatment with sodium sulfate. Purification was performed by column chromatograph to give the target compound 2-(N,N-dimethylamino)-5-iodopyridine (100, 603 mg, 57percent).¹H NMR (400 MHz, CDCl₃) δ 3.08 (s, 6H), 6.34 (d, J=8.4 Hz, 1H), 7.60 (dd, J=8.8, 2.4 Hz, 1H), 8.27 (d, J=2.4 Hz, 1H); ¹³C NMR (100 MHz, CDCl₃) δ 38.1, 105.9, 107.1, 139.2, 148.3, 157.7.

Reference： [1] Patent: US2010/261727, 2010, A1, . Location in patent: Page/Page column 23-24

2
[ 20511-12-0 ]
[ 74-88-4 ]
[ 380381-36-2 ]

Yield	Reaction Conditions	Operation in experiment
2086 mg	Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5 h; Inert atmosphere; Cooling with ice Stage #2: Cooling with ice	Under an argon atmosphere, after a N,N-dimethylformamide solution (20 mL) of 5-iodo-2-aminopyridine (11) (2200 mg, 10.0 mmol) was cooled with ice, sodium hydride (60percent oil, 1200 mg, 30.0 mmol) was added thereto. The reaction liquid was heated to room temperature, and stirred for 30 minutes. The reaction liquid was cooled with ice, and, after methyl iodide (4258 mg, 30.0 mmol) was added thereto, the reaction liquid was heated to room temperature. After the disappearance of the raw material, the reaction liquid was added in water and stirred, and the organic layer was extracted with ethyl acetate. After the organic layer was washed with water and saturated saline water and dried with anhydrous sodium sulphate, the solvent was distillated under reduced pressure. By refining the residue by column chromatography (developing solvent: heptane/ethyl acetate = 99/1 → 24/1), 2086 mg of the title compound (12) was obtained.

Reference： [1] Patent: WO2005/90333, 2005, A1, . Location in patent: Page/Page column 77-78
[2] Patent: EP2767532, 2014, A1, . Location in patent: Paragraph 0268

3
[ 5683-33-0 ]
[ 380381-36-2 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2013, vol. 50, # 5, p. 1031 - 1038

4
[ 20511-12-0 ]
[ 50-00-0 ]
[ 380381-36-2 ]

Reference： [1] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9326 - 9333

[ 380381-36-2 ] Synthesis Path-Downstream 1~15

1
diazotized 5-amino-2-dimethylamino-pyridine [ No CAS ]
[ 380381-36-2 ]

Reference： [1]Chemische Berichte,1928,vol. 61,p. 430
Chemische Berichte,1929,vol. 62,p. 3053

3
[ 20511-12-0 ]
[ 74-88-4 ]
[ 380381-36-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In DMF (N,N-dimethyl-formamide); for 14.0h;	Example 24: N (5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3- [4- (6- dimethylamino-pyridin-3-yl)- [1, 2,3] triazol-1-yl]-4-methyl-benzamide; To a solution of 2-amino-5-iodopyridine (1.00 g ; 4.55 mmol) in 10 mL of DMF was added 545 mg of 60% NaH (13.6 mmol) and 0.85 mL of iodomethane (13.6 mmol). The mixture was stirred for 14h, and the mixture was neutralized with 1M HOAc. The mixture was extracted with Et2O, the extract was washed with water and brine, dried with MgS04, filtered, and concentrated. Chromatography (0-25% EtOAc in hexanes) provided 700 mg (2.82 mmol) of (5-iodo-pyridin-2-yl)-dimethyl-amine.
2086 mg		Under an argon atmosphere, after a N,N-dimethylformamide solution (20 mL) of 5-iodo-2-aminopyridine (11) (2200 mg, 10.0 mmol) was cooled with ice, sodium hydride (60% oil, 1200 mg, 30.0 mmol) was added thereto. The reaction liquid was heated to room temperature, and stirred for 30 minutes. The reaction liquid was cooled with ice, and, after methyl iodide (4258 mg, 30.0 mmol) was added thereto, the reaction liquid was heated to room temperature. After the disappearance of the raw material, the reaction liquid was added in water and stirred, and the organic layer was extracted with ethyl acetate. After the organic layer was washed with water and saturated saline water and dried with anhydrous sodium sulphate, the solvent was distillated under reduced pressure. By refining the residue by column chromatography (developing solvent: heptane/ethyl acetate = 99/1 ? 24/1), 2086 mg of the title compound (12) was obtained.

Reference： [1]Patent: WO2005/90333,2005,A1 .Location in patent: Page/Page column 77-78
[2]Patent: EP2767532,2014,A1 .Location in patent: Paragraph 0268

4
[ 20511-12-0 ]
[ 50-00-0 ]
[ 380381-36-2 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 9326 - 9333

5
[ 380381-36-2 ]
[ 100-53-8 ]
[ 1083329-64-9 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 9326 - 9333

6
[ 380381-36-2 ]
[ 100-46-9 ]
[ 1083329-54-7 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 9326 - 9333

7
[ 380381-36-2 ]
[ 100-51-6 ]
[ 1083329-09-2 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 9326 - 9333

8
[ 280116-78-1 ]
[ 74-88-4 ]
[ 380381-36-2 ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium carbonate; In ISOPROPYLAMIDE; at 90.0℃; for 24.0h;	The obtained 2-(N-monomethylamino)-5-iodopyridine (99, 1.00 g, 4.27 mmol), potassium carbonate (2.95 g, 21.36 mmol) and iodomethane (145 mg, 8.546 mmol) were dissolved in dimethylacetamide (30 mL), and the reaction mixture was heated at 90 C. for 24 hours, followed by adding water. Organic compounds were extracted with ethyl acetate and evaporated after a treatment with sodium sulfate. Purification was performed by column chromatograph to give the target compound 2-(N,N-dimethylamino)-5-iodopyridine (100, 603 mg, 57%).1H NMR (400 MHz, CDCl3) delta 3.08 (s, 6H), 6.34 (d, J=8.4 Hz, 1H), 7.60 (dd, J=8.8, 2.4 Hz, 1H), 8.27 (d, J=2.4 Hz, 1H); 13C NMR (100 MHz, CDCl3) delta 38.1, 105.9, 107.1, 139.2, 148.3, 157.7.

Reference： [1]Patent: US2010/261727,2010,A1 .Location in patent: Page/Page column 23-24

9
[ 5683-33-0 ]
[ 380381-36-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,2013,vol. 50,p. 1031 - 1038

10
[ 380381-36-2 ]
[ 107-19-7 ]
[ 1565798-14-2 ]

Yield	Reaction Conditions	Operation in experiment
1340 mg	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine;Inert atmosphere;	(Step 2: Synthesis of Compound (13)) Under an argon atmosphere, copper iodide (191 mg, 1.00 mmol), 2-propyn-1-ol (939 mg, 16.75 mmol) and dichlorobis (triphenylphosphine) palladium (II) (118 mg, 0.17 mmol) were added in a triethylamine solution (8.17 mL, 58.61 mmol) of the compound (12) (2077 mg, 8.37 mmol), and the resultant solution was stirred. After the disappearance of the raw material was confirmed, the reaction liquid was filtered, and the solvent was distillated under reduced pressure. By refining the residue by column chromatography (developing solvent: heptane/ethyl acetate = 19/1 ? 1/1), 1340 mg of the title compound (13) was obtained.

Reference： [1]Patent: EP2767532,2014,A1 .Location in patent: Paragraph 0269

11
[ 380381-36-2 ]
[ 1565798-15-3 ]

Reference： [1]Patent: EP2767532,2014,A1

12
[ 380381-36-2 ]
C₂₁H₁₉N₃O [ No CAS ]

Reference： [1]Patent: EP2767532,2014,A1

13
[ 380381-36-2 ]
[ 1565797-24-1 ]

Reference： [1]Patent: EP2767532,2014,A1

14
2-ethynyl-1,3-difluorobenzene [ No CAS ]
[ 380381-36-2 ]
5-((2,6-difluorophenyl)ethynyl)-N,N-dimethylpyridin-2-amine [ No CAS ]

Reference： [1]MedChemComm,2018,vol. 9,p. 87 - 99

15
[ 380381-36-2 ]
carboxy MIDA boronate [ No CAS ]
[ 171290-53-2 ]
3-(3-(6-(dimethylamino)pyridin-3-yl)-3-oxoprop-1-yn-1-yl)benzonitrile [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2021,vol. 60,p. 4342 - 4349
Angew. Chem.,2021,vol. 133,p. 4388 - 4395,8

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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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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. 380381-36-2 ] {[proInfo.proName]}

Quality Control of [ 380381-36-2 ]

Related Doc. of [ 380381-36-2 ]

Product Details of [ 380381-36-2 ]

Calculated chemistry of [ 380381-36-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 380381-36-2 ]

Application In Synthesis of [ 380381-36-2 ]

[ 380381-36-2 ] Synthesis Path-Upstream 1~4

[ 380381-36-2 ] Synthesis Path-Downstream 1~15

Related Functional Groups of [ 380381-36-2 ]

Amines

Related Parent Nucleus of [ 380381-36-2 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 380381-36-2 ]

Related Parent Nucleus of
[ 380381-36-2 ]