[ CAS No. 1217090-32-8 ] {[proInfo.proName]}

Name: 1217090-32-8|N-Methyl-5-bromo-4,7-diazaindole|98%
Brand: Ambeed
SKU: A160971
Rating: 92 (29 reviews)

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3d Animation Molecule Structure of 1217090-32-8

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Quality Control of [ 1217090-32-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1217090-32-8 ]

SDS Specification

Alternatived Products of [ 1217090-32-8 ]

Product Details of [ 1217090-32-8 ]

CAS No. :	1217090-32-8	MDL No. :	MFCD12964054
Formula :	C₇H₆BrN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	212.05	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 1217090-32-8 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.14
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.49
TPSA :	30.71 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) :	-6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.05
Log Po/w (XLOGP3) :	1.31
Log Po/w (WLOGP) :	1.73
Log Po/w (MLOGP) :	0.87
Log Po/w (SILICOS-IT) :	1.62
Consensus Log Po/w :	1.51

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.59
Solubility :	0.551 mg/ml ; 0.0026 mol/l
Class :	Soluble
Log S (Ali) :	-1.56
Solubility :	5.9 mg/ml ; 0.0278 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.96
Solubility :	0.233 mg/ml ; 0.0011 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.96

Safety of [ 1217090-32-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1217090-32-8 ]

* 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 [ 1217090-32-8 ]

[ 1217090-32-8 ] Synthesis Path-Downstream 1~6

1
[ 1471257-05-2 ]
[ 1217090-32-8 ]
[ 2219364-90-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-bromo-5-methyl-5H-pyrrolo[2,3-b]pyrazine With n-butyllithium In hexane; toluene at -78℃; for 1.5h; Stage #2: With zinc(II) chloride In tetrahydrofuran; 2-methyltetrahydrofuran; hexane; toluene at -78 - 20℃; for 3h; Stage #3: ethyl (S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-(tert-butoxy)acetate With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran; 2-methyltetrahydrofuran; hexane; toluene at 60℃; for 3h; Inert atmosphere;	19 Preparation of ethyl (S)-2-(tert-butoxy)-2-(7-(4-chlorophenyl)-5-methyl-2-(5-methyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)benzo[d]thiazol-6-yl)acetate To an oven-dried round bottom flask was charged 2-bromo-5-methyl-5H-pyrrolo[2,3-b]pyrazine (896 mg, 4.23 mmol, 2.00 equiv), which was then dissolved in 3:1 toluene:hexanes (12 mL). The reaction solution was then cooled to -78° C. and a solution of n-butyllithium in hexanes (2.50 M, 1.86 mL, 4.65 mmol, 2.20 equiv) was added dropwise. After stirring for 1.5 h, a solution of zinc chloride in 2-methyltetrahydrofuran (1.90 M, 2.56 mL, 4.86 mmol, 2.30 equiv) was then added, followed by 10 mL of tetrahydrofuran. After stirring at -78° C. for 25 min, the reaction mixture was warmed to 0° C. and stirred for an additional 35 min. The reaction was then allowed to warm to room temperature and was stirred for an additional 2 h. Ethyl (S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-(tert-butoxy)acetate (1.05 g, 2.11 mmol, 1.00 equiv) and Pd(PPh3)4(244 mg, 0.211 mmol, 0.10 equiv) were then added. The reaction mixture was sparged with argon for 10 min and subsequently heated to 60° C. After stirring for 3 h, the reaction was cooled to room temperature. 1 M hydrochloric acid was added until all solids dissolved. Saturated aqueous NaHCO3 was added until pH˜7 was reached. The reaction was then diluted with EtOAc (30 mL) and the organic and aqueous layers were separated. The aqueous layer was extracted with additional EtOAc (3*15 mL) and the organic layers were all combined, washed with brine (30 mL), dried over anhydrous MgSO4, filtered, and concentrated. The crude product was purified via CombiFlash (Peeke Scientific, silica gel, gradient: 0-100% EtOAc/hex) to afford the desired product as a pale yellow flocculent solid. LCMS-ESI+: calc'd for C29H30ClN4O3S: 549.17 [M+H]+; found: 549.19.

Reference： [1]Current Patent Assignee: GILEAD SCIENCES INC - US2018/118734, 2018, A1 Location in patent: Paragraph 0390; 0391

2
[ 5049-61-6 ]
[ 1217090-32-8 ]
[ 2375478-72-9 ]

Yield	Reaction Conditions	Operation in experiment
55%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 40h; Inert atmosphere;	BO /V-{5-Methyl-5H-pyrrolo[2,3-b]pyrazin-2-yl}-/V-({5-[5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl]thiophen-2-yl}methyl)pyrazin-2-amine Under Ar(g), to a mixture of pyrazin-2-amine (1) (123mg, 1.3mmol), N- methyl-5-bromo-4,7-diazaindole (2) (250mg, 1.2mmol), Cs2C03 (0.77g, (0493) 2.4mmol) was added degassed dry 1 ,4-dioxane (13mL). The reaction mixture was then flushed with Ar(g) for 1 min before Pd2(dba)3 (54mg, 0.06mmol) and Xantphos (75mg, 0.13mmol) were added. The reaction mixture was heated up to 90°C for 40h. It was then cooled down to rt and concentrated in vacuo, CH2CI2 (15mL) and H20 (15mL) were added. The organic phase was separated and the water layer was extracted with CH2CI2 (15mL). The organic layers were combined and Pd-scavenger (MP-TMT, ~400mg, 1.3mmol/g) was added. This was shaken for several hours followed by filtration. The filtrate was concentrated in vacuo, dissolved in DMSO (4mL) and purified by basic prep LCMS to yield (3) as a solid (147mg, 55%). (0494) LCMS (ES): Found 227.2 [M+Hf.

Reference： [1]Current Patent Assignee: KARUS THERAPEUTICS LIMITED - WO2019/166824, 2019, A1 Location in patent: Page/Page column 65

3
[ 1217090-32-8 ]
[ 2375476-29-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 40 h / 90 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.08 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: KARUS THERAPEUTICS LIMITED - WO2019/166824, 2019, A1

4
[ 875781-43-4 ]
[ 74-88-4 ]
[ 1217090-32-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 2-bromo-5H-pyrrolo[2,3-b]pyrazine With sodium hydride In tetrahydrofuran at 0 - 18℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran at 18℃; for 2h;	2-bromo-5-methyl-5H-pyrrolo[2,3-b]pyrazine: NaH (20.2 mg, 0.505 mmol, 60% purity) was added to a solution of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (50 mg, 0.253 mmol) in THF (6 mL) at 0°C and the mixture stirred at 18°C for 0.5 h. Iodomethane (53.8 mg, 0.379 mmol) was added and the mixture was stirred at 18°C for 2 h. The reaction was quenched by sat. ar/.NH4Cl (2 mL), diluted with 0 (10 mL) and extracted with EtOAc (3 x 20 mL). The combined organics were washed with brine, dried (Na2S04) and evaporated to dryness in vacuo. The residue was purified by prep- TLC (petroleum ether/EtOAc; 15: 1 to 5: 1) to give the title compound as a yellow solid (38.9 mg, 72%). 1H NMR (400 MHz, CDCI3) d: 8.31 (s, 1H), 7.47 (d, 7=3.2 Hz, 1H), 6.62 (d, 7=4.0 Hz, 1H), 3.90 (s, 3H).
64%	Stage #1: 2-bromo-5H-pyrrolo[2,3-b]pyrazine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;
59%	Stage #1: 2-bromo-5H-pyrrolo[2,3-b]pyrazine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;

Reference： [1]Current Patent Assignee: BIOGEN IDEC INC. - WO2020/163193, 2020, A1 Location in patent: Paragraph 00236
[2]Liu, Shuai; Huang, Yangen; Wang, Juan; Qing, Feng-Ling; Xu, Xiu-Hua [Journal of the American Chemical Society, 2022, vol. 144, # 4, p. 1962 - 1970]
[3]Wang, Juan; Liu, Shuai; Huang, Yangen; Xu, Xiu-Hua; Qing, Feng-Ling [Chemical Communications, 2022, vol. 58, # 9, p. 1346 - 1349]

5
[ 1217090-32-8 ]
[ 2760510-18-5 ]
[ 2760510-47-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	With tris[2-phenylpyridinato-C²,N]iridium(III) In acetonitrile at 20℃; for 8h; Sealed tube; Inert atmosphere; Irradiation; regioselective reaction;

Reference： [1]Wang, Juan; Liu, Shuai; Huang, Yangen; Xu, Xiu-Hua; Qing, Feng-Ling [Chemical Communications, 2022, vol. 58, # 9, p. 1346 - 1349]

6
[ 1217090-32-8 ]
[ 2758435-22-0 ]
[ 2758435-61-7 ]

Yield	Reaction Conditions	Operation in experiment
55%	With fac-tris(2-phenylpyridinato-N,C₂')iridium(III) In 1,2-dichloro-ethane at 20℃; for 18h; Irradiation; Inert atmosphere;

Reference： [1]Liu, Shuai; Huang, Yangen; Wang, Juan; Qing, Feng-Ling; Xu, Xiu-Hua [Journal of the American Chemical Society, 2022, vol. 144, # 4, p. 1962 - 1970]

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[ 1217090-32-8 ]

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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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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.
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H221	Flammable gas
H222	Extremely flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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H250	Catches fire spontaneously if exposed to air
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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. 1217090-32-8 ] {[proInfo.proName]}

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Calculated chemistry of [ 1217090-32-8 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 1217090-32-8 ]

[ 1217090-32-8 ] Synthesis Path-Downstream 1~6

Related Functional Groups of [ 1217090-32-8 ]

Bromides

Related Parent Nucleus of [ 1217090-32-8 ]

Other Aromatic Heterocycles

Precautionary Statements-General

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Environmental hazards

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Related Functional Groups of
[ 1217090-32-8 ]

Related Parent Nucleus of
[ 1217090-32-8 ]