[ CAS No. 88625-24-5 ] {[proInfo.proName]}

Name: 88625-24-5|5-Chloropyrazine-2-carbaldehyde|97%
Brand: Ambeed
SKU: A102532
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Quality Control of [ 88625-24-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 88625-24-5 ]

Product Details of [ 88625-24-5 ]

CAS No. :	88625-24-5	MDL No. :	MFCD10697774
Formula :	C₅H₃ClN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UIKDIRUDGAKSGG-UHFFFAOYSA-N
M.W :	142.54	Pubchem ID :	21698067
Synonyms :

Calculated chemistry of [ 88625-24-5 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	32.43
TPSA :	42.85 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) :	-6.79 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.71
Log Po/w (XLOGP3) :	0.54
Log Po/w (WLOGP) :	0.94
Log Po/w (MLOGP) :	-0.84
Log Po/w (SILICOS-IT) :	1.72
Consensus Log Po/w :	0.61

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.49
Solubility :	4.6 mg/ml ; 0.0323 mol/l
Class :	Very soluble
Log S (Ali) :	-1.01
Solubility :	13.9 mg/ml ; 0.0974 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.19
Solubility :	0.916 mg/ml ; 0.00643 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.72

Safety of [ 88625-24-5 ]

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 [ 88625-24-5 ]

* 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 [ 88625-24-5 ]
Downstream synthetic route of [ 88625-24-5 ]

[ 88625-24-5 ] Synthesis Path-Upstream 1~4

1
[ 88625-24-5 ]
[ 72788-94-4 ]

Reference： [1] Patent: WO2009/134668, 2009, A2, . Location in patent: Page/Page column 29; 30

2
[ 33332-25-1 ]
[ 88625-24-5 ]

Yield	Reaction Conditions	Operation in experiment
68%	With diisobutylaluminium hydride In tetrahydrofuran; toluene at -55℃; for 1 h; Inert atmosphere	Diisobutylaluminium hydride (1.0 M in toluene; 6.4 mL, 6.40 mmol) was added dropwise to a cooled solution of methyl 5-chloropyrazine-2-carboxylate (690 mg, 4.00 mmol) in THF (13.6 mL) at -55 °C. The reaction was stirred under these conditions for 1 hour and then quenched by addition of saturated aqueous NH4C1 (25 mL) and EtOAc (25 mL). An emulsion formed and 2N aqueous HC1 was added to clear the emulsion (5 mL). The layers were separated, and the aqueous layer was extracted with EtOAc. The organic layerwas washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by flash silica chromatography, elution gradient 0 to 50percent EtOAc in heptane. Product fractions were evaporated to dryness to afford 5-chloropyrazine-2-carbaldehyde (385 mg, 68percent) as a beige solid. ‘H NMR (500 MHz, CDC13, 27 °C) 8.75 (1H, d), 8.96 (1H, d), 10.15 (1H, d).

Reference： [1] Patent: WO2018/19793, 2018, A1, . Location in patent: Page/Page column 147; 148
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 13, p. 5344 - 5354
[3] Patent: WO2012/81736, 2012, A1, . Location in patent: Page/Page column 91-92
[4] Patent: WO2018/93569, 2018, A1,

3
[ 72788-94-4 ]
[ 88625-24-5 ]

Yield	Reaction Conditions	Operation in experiment
50.7%	With manganese(IV) oxide In chloroform for 2 h; Reflux	To a solution of Intermediate 112A (2.00 g, 13.84 mmol) in CHCl3 (20 mL) was added active manganese dioxide (4.81 g, 55.3 mmol) and the resulting suspension was refluxed for 2 h. The reaction mixture was cooled to ambient temperature, filtered through Celite® and washed with CHCl₃ (200 mL). The combined filtrates were washed with brine (200 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Redisep-24 g, 20-30 percent EtOAc/ n-hexane) to obtain Intermediate 112B (1.00 g, 50.70percent) as a white solid.¹H NMR (400 MHz, DMSO-d6) δ ppm 8.98 (d, J = 1.51 Hz, 1 H), 9.04 (d, J = 1.51 Hz, 1 H), 10.07 (s, 1 H). LCMS: The compound did not ionize well.

Reference： [1] Patent: WO2018/93569, 2018, A1, . Location in patent: Page/Page column 196Intermediate 112B: 5-chloropyrazine-2-carbaldeh

4
[ 36070-80-1 ]
[ 88625-24-5 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 13, p. 5344 - 5354

[ 88625-24-5 ] Synthesis Path-Downstream 1~32

1
[ 88625-24-5 ]
[ 72788-94-4 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; sodium tetrahydroborate; at 0 - 20℃; for 3h;	A solution of 5-chloropyrazine-2-carbaldehyde (5.20 g, 36.5 mmol) in 50 mL of methanol was cooled to O0C. Sodium borohydride (1.45 g, 38.3 mmol) was added and the reaction mixture was allowed to stir at ambient temperature for 3 hour. Saturated aqueous ammonium chloride (5 mL) was added, and the methanol was removed in vacuo. The resulting residue was dissolved in ethyl acetate (50 mL) and washed with aqueous sodium bicarbonate (2 x 50 mL) and brine (50 mL). <n="32"/>The combined organic extracts were dried, filtered and concentrated in vacuo to provide the title compound that gave a proton NMR spectra consistent with theory.

Reference： [1]Patent: WO2009/134668,2009,A2 .Location in patent: Page/Page column 29; 30

2
[ 88625-24-5 ]
[ 1356386-08-7 ]
[ 1356386-27-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 60℃; for 18h;	Step 2. To the residue from Step 1 was added solid sodium bicarbonate (1012 mg, 5 equiv) and <strong>[88625-24-5]5-chloropyrazine-2-carbaldehyde</strong> (400 mg, 1.2 equiv) and DMF (8 mL). The mixture was stirred at 60 C for 18 hours then cooled and poured into water and the mixture neutralized with 1 M HCl. Extraction first with ether then with ethyl acetate gave an organic fraction that was washed four times with water, then dried on anhydrous sodium sulfate, filtered and concentrated in vacuo to give an orange solid that was carried forward crude: [MH]+ m z 318.

Reference： [1]Patent: WO2012/9217,2012,A1 .Location in patent: Page/Page column 63

3
[ 88625-24-5 ]
[ 1383001-11-3 ]

Reference： [1]Patent: WO2012/81736,2012,A1

4
[ 88625-24-5 ]
[ 1383001-13-5 ]
[ 1383001-12-4 ]

Reference： [1]Patent: WO2012/81736,2012,A1

5
[ 88625-24-5 ]
[ 1383001-14-6 ]
[ 1383001-15-7 ]

Reference： [1]Patent: WO2012/81736,2012,A1

6
[ 88625-24-5 ]
[ 1383001-16-8 ]

Reference： [1]Patent: WO2012/81736,2012,A1

7
[ 88625-24-5 ]
[ 1383000-29-0 ]
[ 1383001-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; N,N-dimethyl-formamide; at 65℃; for 2h;Inert atmosphere;	2) N,N-dimethylformamide (10 mL) was added to <strong>[88625-24-5]5-chloropyrazine-2-carbaldehyde</strong> (500 mg), methyl 2,2-dimethyl-3-[4-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)pyridin-2-yl]oxy}propanoate (1410 mg) and 2N aqueous sodium carbonate solution (5.26 mL), and after replacing the atmosphere with nitrogen, palladium chloride (dppf) methylene chloride complex (143 mg) was added to the mixture and the resulting mixture was stirred at 65C for 2 hours. To the reaction mixture were added ethyl acetate and water, and the liquids were separated. After filtration with Celite, the organic layer was separated, washed with water and then with a saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=100:0 to 70:30) to obtain methyl 3-[5-(5-formylpyrazin-2-yl)-4-methylpyridin- 2-yl]oxy}-2,2-dimethylpropanoate (855 mg). MS (m/z): 330 [M+H]+

Reference： [1]Patent: WO2012/81736,2012,A1 .Location in patent: Page/Page column 92

8
[ 33332-25-1 ]
[ 88625-24-5 ]

Yield	Reaction Conditions	Operation in experiment
68%	With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -55℃; for 1h;Inert atmosphere;	Diisobutylaluminium hydride (1.0 M in toluene; 6.4 mL, 6.40 mmol) was added dropwise to a cooled solution of methyl 5-chloropyrazine-2-carboxylate (690 mg, 4.00 mmol) in THF (13.6 mL) at -55 C. The reaction was stirred under these conditions for 1 hour and then quenched by addition of saturated aqueous NH4C1 (25 mL) and EtOAc (25 mL). An emulsion formed and 2N aqueous HC1 was added to clear the emulsion (5 mL). The layers were separated, and the aqueous layer was extracted with EtOAc. The organic layerwas washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in heptane. Product fractions were evaporated to dryness to afford 5-chloropyrazine-2-carbaldehyde (385 mg, 68%) as a beige solid. ?H NMR (500 MHz, CDC13, 27 C) 8.75 (1H, d), 8.96 (1H, d), 10.15 (1H, d).
		Example 95 [0308] [Formula 107]CI xj - ~ CI' [0309] 1) In tetrahydrofuran (66 mL) was dissolved methyl 5-chloropyrazine-2-carboxylate (3.3 g), and 1M diisobutylaluminum hydride/hexane solution (38.3 mL) was added dropwise to the solution under nitrogen atmosphere at -70C or lower over 10 minutes, and the resulting mixture was further stirred for 10 minutes. At -60C or lower, 1M diisobutylaluminum hydride/hexane solution (31.3 mL) was added dropwise to the mixture over 20 minutes, and the mixture was further stirred at -70C or lower for 1 hour. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, and after stirring at room temperature, filtered with Celite. The filtrate was extracted with ethyl acetate, washed with a saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=100:0 to 80:20) to obtain 5-chloropyrazine-2-carbaldehyde (970 mg). MS (m/z): 142/144 [M+H]+

Reference： [1]Patent: WO2018/19793,2018,A1 .Location in patent: Page/Page column 147; 148
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 5344 - 5354
[3]Patent: WO2012/81736,2012,A1 .Location in patent: Page/Page column 91-92
[4]Patent: WO2018/93569,2018,A1

9
[ 88625-24-5 ]
[ 1388144-31-7 ]
[ 1388144-33-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In 1,2-dimethoxyethane; ethanol; at 120℃; for 0.333333h;Inert atmosphere; Microwave irradiation;	Intermediate 19 ethyl { l-i"5-("5-formylpyrazin-2-vl)pyrimidin-2-yl]piperidin-4-vnacetateTo a mixture of ethyl {l-[5-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yi)pyrimidin-2- yl]piperidin-4-yl} acetate (Intermediate 18), 0.5 g, 1.33 mmol, 1.00 equiv), 5-chJoropyrazine-2- carbaldehyde (0.377 g, 2.66 mmol, 2.00 equiv), tetrakis (0.231 g, 0.2 mmol, 0.15 equiv) and Na2P¾ (2.66 mL, 2.0 M, 4.0 equiv) was added DME (13.0 mL)/EtOH (8.0 mL). The reaction mixture was degassed and purged with nitrogen with stirring for 10 min followed by MW at 120 C for 20 min. Solvent evaporated and mixture diluted with water and extracted 3x with EtOAc. The organic layers were combined, dried over MgS04 and concentrated in vacuo. The residue was purified by eluting through a silica gel column with a 0-70% EtOAc/Hexane solvent system to provide product ethyl { l-[5-(5-formylpyrazin-2-yi)pyrimidin-2-yl]piperidin-4-yl}acetate. LC- MS (ES, m/z) CisH21N503: 355; Found: 356 [M+H)+.

Reference： [1]Patent: WO2012/96813,2012,A1 .Location in patent: Page/Page column 50

10
[ 109-01-3 ]
[ 88625-24-5 ]
2-chloro-5-((4-methylpiperazin-1-yl)methyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
285 mg	With sodium tris(acetoxy)borohydride; In acetonitrile; at 0 - 35℃; for 4h;	Sodium triacetoxyborohydride (870 mg) was added to a solution of <strong>[88625-24-5]5-chloropyrazine-2-carbaldehyde</strong> (390 mg) and 1-methylpiperazine (0.335 mL) in acetonitrile (10 mL) at 0C. The reaction mixture was stirred at room temperature for 4 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, hexane/ethyl acetate) to give the title compound (285 mg). MS (ESI+) : [M+H] +226.8
290 mg	With sodium tris(acetoxy)borohydride; In acetonitrile; at 0 - 20℃; for 4h;	Sodium triacetoxyborohydride (870 mg) was added to a solution of <strong>[88625-24-5]5-chloropyrazine-2-carbaldehyde</strong> (390 mg) and 1-methylpiperazine (0.34 mL) in acetonitrile (10 mL) at 0 C. The reaction mixture was stirred at room temperature for 4 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (290 mg). MS(ESI+): [M+H]+ 226.8.

Reference： [1]Patent: EP2818473,2014,A1 .Location in patent: Paragraph 0557; 0558
[2]Patent: US2016/159773,2016,A1 .Location in patent: Paragraph 1142-1144

11
[ 88625-24-5 ]
[ 1196473-37-6 ]
C₁₂H₉BN₂O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5344 - 5354

12
[ 36070-80-1 ]
[ 88625-24-5 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5344 - 5354

13
[ 88625-24-5 ]
(E)-5-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yloxy)pyrazine-2-carbaldehyde oxime [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5344 - 5354

14
[ 88625-24-5 ]
6-(5-((dimethylamino)methyl)pyrazin-2-yloxy)benzo[c][1,2]oxaborol-1(3H)-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5344 - 5354

15
[ 496807-97-7 ]
[ 88625-24-5 ]
2-chloro-5-[(3,3-difluoropiperidin-1-yl)methyl]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium tris(acetoxy)borohydride; triethylamine; In 1,2-dichloro-ethane; at 20℃;	3,3-Difluoropiperidine hydrochloride [CAS RN: 496807-97-7] (531 mg, 3.37 mmol,1.6 eq), 5-chloropyrazine-2-carbaldehyde [CAS RN: 88625-24-5] (300 mg,2.11 mmol, 1.0 eq) and sodium triacetoxyborohydride (1.43 g, 6.74 mmol,3.2 eq) were suspended in 20 mL 1,2-dichloroethane. Then, triethylamine (0.59 mL, 4.21 mmol, 2.0 eq) was added and the reaction mixture was stirred at rt overnight. Then, water was added. After stirring for 10 mm, the resulting phases were separated by the use of a Whatman filter. The volatile components of theorganic phase were removed in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 25 g SNAP cartridge: hexane/ethyl acetate 9/1 -> hexane/ethyl acetate 1/1) to give 340 mg (58% yield of theory) of the title compound.UPLC-MS (Method 2): R = 1.09 mm; MS (EI0): m/z = 248 [M+H].1H-NMR (400 MHz, DMSO-d6): oe [ppm] = 1.64 (m, 2H), 1.86 (m, 2H), 2.73 (t, 2H),3.78 (5, 2H), 8.49 (d, 1H), 8.74 (d, 1H), 2H?s obscured by solvent signal.

Reference： [1]Patent: WO2015/113927,2015,A1 .Location in patent: Page/Page column 213

16
[ 2730-67-8 ]
[ 88625-24-5 ]
N-[(5-chloropyrazin-2-yl)methyl]-2,2,2-trifluoro-N-methylethanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With sodium tris(acetoxy)borohydride; triethylamine; In 1,2-dichloro-ethane; at 20℃;	2,2,2-Trif[uoro-N-methy[ethanamine [CAS RN: 2730-67-8] (254 mg, 2.25 mmo[,1.6 eq), 5-ch[oropyrazine-2-carba[dehyde [CAS RN: 88625-24-5] (200 mg,1 .40 mmo[, 1 .0 eq) and sodium triacetoxyborohydride (952 mg, 4.49 mmo[,3.2 eq) were suspended in 20 mL 1,2-dichioroethane. Then, triethylamine (0.39mL, 2.81 mmo[, 2.0 eq) was added and the reaction mixture was stirred at rt overnight. Then, water was added. After stirring for 10 mm, the resulting phases were separated by the use of a Whatman filter. The volatile components of the organic phase were removed in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 25 g SNAP cartridge: hexane/ethyl acetate9/1 -> hexane/ethyl acetate 1/1) to give 100 mg (29% yield of theory) of the title compound.UPLC-MS (Method 1): R = 1.13 mm; MS (EI0): m/z = 240 [M+H].1H-NMR (400 MHz, DMSO-d6): oe [ppm] = 2.39 (5, 3H), 3.37 (q, 2H), 3.92 (5, 2H),8.50 (d, 1H), 8.74 (d, 1H).

Reference： [1]Patent: WO2015/113927,2015,A1 .Location in patent: Page/Page column 218

17
3-fluoroazetidine hydrochloride [ No CAS ]
[ 88625-24-5 ]
2-chloro-5-[(3-fluoroazetidin-1-yl)methyl]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium tris(acetoxy)borohydride; triethylamine; In 1,2-dichloro-ethane; at 20℃;	3-Fluoroazetidine hydrochloride [CAS RN: 617718-46-4] (250 mg, 2.25 mmol,1.6 eq), <strong>[88625-24-5]5-chloropyrazine-2-carbaldehyde</strong> [CAS RN: 88625-24-5] (200 mg,1 .40 mmol, 1 .0 eq) and sodium triacetoxyborohydride (0.952 g, 4.49 mmol,3.2 eq) were suspended in 17 mL 1,2-dichloroethane. Then, triethylamine (0.39mL, 2.81 mmol, 2.0 eq) was added and the reaction mixture was stirred at rt overnight. Then, water was added. After stirring for 10 mm, the resulting phases were separated by the use of a Whatman filter. The volatile components of the organic phase were removed in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 25 g SNAP cartridge: hexane/ethyl acetate9/1 -> hexane/ethyl acetate 1/1) to give 180 mg (50% yield of theory) of the title compound.UPLC-MS (Method 2): R = 0.79 mm; MS (EI0): m/z = 202 [M+H].

Reference： [1]Patent: WO2015/113927,2015,A1 .Location in patent: Page/Page column 210; 211

18
[ 88625-24-5 ]
[ 163457-23-6 ]
2-chloro-5-[(3,3-difluoropyrrolidin-1-yl)methyl]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With sodium tris(acetoxy)borohydride; triethylamine; In 1,2-dichloro-ethane; at 20℃;	3,3-Difluoropyrrolidine hydrochloride [CAS RN: 163457-23-6] (415 mg,2.89 mmol, 1.6 eq), <strong>[88625-24-5]5-chloropyrazine-2-carbaldehyde</strong> [CAS RN: 88625-24-5] (258mg, 1.81 mmol, 1.0 eq) and sodium triacetoxyborohydride (1.12 g, 5.78 mmol,3.2 eq) were suspended in 17 mL 1,2-dichloroethane. Then, triethylamine (0.50 mL, 3.61 mmol, 2.0 eq) was added and the reaction mixture was stirred at rt overnight. Then, water was added and the resulting phases were separated by the use of a Whatman filter. The volatile components of the organic phase wereremoved in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 25 g SNAP cartridge: hexane/ethyl acetate 9/1 -> hexane/ethyl acetate 1/1) to give 250mg (57% yield of theory) of the title compound.UPLC-MS (Method 1): R = 0.70 mm; MS (EI0): m/z = 234 [M+H].

Reference： [1]Patent: WO2015/113927,2015,A1 .Location in patent: Page/Page column 210

19
[ 88625-24-5 ]
4,4-difluoropiperidine hydrochloride [ No CAS ]
2-chloro-5-[(4,4-difluoropiperidin-1-yl)methyl]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium tris(acetoxy)borohydride; triethylamine; In 1,2-dichloro-ethane; at 20℃;	4,4-Difluoropiperidine hydrochloride [CAS RN: 144230-52-4] (495 mg, 3.14 mmol,1.6 eq), <strong>[88625-24-5]5-chloropyrazine-2-carbaldehyde</strong> [CAS RN: 88625-24-5] (280 mg,3.14 mmol, 1.0 eq) and sodium triacetoxyborohydride (1.32 g, 6.29 mmol,3.2 eq) were suspended in 17 mL 1,2-dichloroethane. Then, triethylamine (0.55mL, 3.93 mmol, 2.0 eq) was added and the reaction mixture was stirred at rtovernight. Then, water was added and the resulting phases were separated bythe use of a Whatman filter. The volatile components of the organic phase wereremoved in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 25 g SNAP cartridge: hexane/ethyl acetate 9/1 -> hexane/ethyl acetate 1/1) to give 320mg (63% yield of theory) of the title compound.UPLC-MS (Method 1): R = 0.56 mm; MS (EI0): m/z = 248 [M+H].

Reference： [1]Patent: WO2015/113927,2015,A1 .Location in patent: Page/Page column 185

20
[ 88625-24-5 ]
N-(3,4-difluorophenyl)-5-({5-[(4,4-difluoropiperidin-1-yl)methyl]pyrazin-2-yl}amino)-3-methyl-1,2-thiazole-4-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/113927,2015,A1

21
[ 88625-24-5 ]
5-({5-[(3,3-difluoroazetidin-1-yl)methyl]pyrazin-2-yl}amino)-N-(3,4-difluorophenyl)-3-methyl-1,2-thiazole-4-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/113927,2015,A1

22
[ 88625-24-5 ]
N-(3,4-difluorophenyl)-3-methyl-5-[(5-[methyl(2,2,2-trifluoroethyl)amino]methyl}pyrazin-2-yl)amino]-1,2-thiazole-4-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/113927,2015,A1

23
[ 288315-03-7 ]
[ 88625-24-5 ]
2-chloro-5-[(3,3-difluoroazetidin-1-yl)methyl]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium tris(acetoxy)borohydride; triethylamine; In 1,2-dichloro-ethane; at 20℃;	3,3-Difluoroazetidine hydrochloride [CAS RN: 288315-03-7] (436 mg, 3.37 mmol,1.6 eq), <strong>[88625-24-5]5-chloropyrazine-2-carbaldehyde</strong> [CAS RN: 88625-24-5] (300 mg,2.11 mmol, 1.0 eq) and sodium triacetoxyborohydride (1.47 g, 6.74 mmol,3.2 eq) were suspended in 20 mL 1,2-dichloroethane. Then, triethylamine (0.59mL, 4.21 mmol, 2.0 eq) was added and the reaction mixture was stirred at rtovernight. Then, water was added and the resulting phases were separated by the use of a Whatman filter. The volatile components of the organic phase were removed in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 25 g SNAP cartridge: hexane/ethyl acetate 9/1 -> hexane/ethyl acetate 1/1) to give 330mg (70% yield of theory) of the title compound.UPLC-MS (Method 1): R = 0.65 mm; MS (EI0): m/z = 220 [M+H].

Reference： [1]Patent: WO2015/113927,2015,A1 .Location in patent: Page/Page column 185; 186

24
[ 88625-24-5 ]
(S)-N-[(1E)-1-(2-[tert-butyl(dimethyl)silyl]oxy}-4-methoxyphenyl)ethylidene]-2-methylpropane-2-sulfinamide [ No CAS ]
(S)-N-[(1E,3S)-3-(5-chloropyrazin-2-yl)-3-hydroxy-1-(2-hydroxy-4-methoxyphenyl)propylidene]-2-methylpropane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42.8%		Example 193A (S)-N-[(1E,3S)-3-(5-chloropyrazin-2-yl)-3-hydroxy-1-(2-hydroxy-4-methoxyphenyl)propylidene]-2-methylpropane-2-sulfinamide A solution of N,N-diisopropylamine (136 muL, 0.958 mmol) in tetrahydrofuran (5 mL) under N2 at -78 C. was treated with 2.5 M n-butyl lithium in hexanes (354 muL, 0.884 mmol), warmed to 0 C., stirred for 15 minutes at 0 C., cooled to -78 C., treated with a solution of Example 190B (394 mg, 1.027 mmol) in tetrahydrofuran (2 mL), stirred at -78 C. for 45 minutes, treated with a solution of <strong>[88625-24-5]5-chloropyrazine-2-carbaldehyde</strong> (CAS No.88625-24-5, 105 mg, 0.737 mmol), stirred at -78 C. for 75 minutes, treated with a solution of acetic acid (84 muL, 1.473 mmol) in tetrahydrofuran (1 mL), warmed to 0 C., treated with 1 m tetrabutylammonium fluoride in tetrahydrofuran (1105 muL, 1.105 mmol), stirred at 0 C. for 90 minutes, diluted with ethyl acetate (75 mL) and washed with saturated aqueous NaHCO3 solution. The ethyl acetate layer was washed with brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel eluting with a gradient of 0 to 100% (over 10 minutes) [1:1 CH2Cl2: ethyl acetate] in [9:1 CH2Cl2: ethyl acetate] to provide the title compound (0.13 g, 0.316 mmol, 42.8% yield) as the second eluting isomer. 1H NMR (500 MHz, CDCl3) delta 13.07 (s, 1H), 8.55 (d, J=1.4 Hz, 1H), 8.45 (dd, J=1.3, 0.6 Hz, 1H), 7.13 (d, J=9.2 Hz, 1H), 6.39 (d, J=2.6 Hz, 1H), 6.23 (dd, J=9.1, 2.6 Hz, 1H), 5.36 (q, J=4.9 Hz, 1H), 4.93 (d, J=4.6 Hz, 1H), 3.86 (dd, J=13.6, 6.4 Hz, 0H), 3.81 (s, 3H), 3.79 (dd, J=13.6, 5.0 Hz, 1H), 1.39 (s, 9H); LC/MS (ESI+) m/z 412 (M+H)+.

Reference： [1]Patent: US2017/15675,2017,A1 .Location in patent: Paragraph 1438

25
[ 88625-24-5 ]
2-chloro-5-(difluoromethyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With diethylamino-sulfur trifluoride; triethylamine tris(hydrogen fluoride); In dichloromethane; at 20℃; for 18h;	To a solution of <strong>[88625-24-5]5-chloropyrazine-2-carbaldehyde</strong> (500 mg, 3.51 mmol) in CH2Cl2 (10 mL) was added (diethylamino)difluorosulfonium tetrafluoroborate (2.0 g, 8.77 mmol) and triethylamine trihydrofluoride (0.57 mL, 3.51 mmol). The reaction mixture was stirred for 18 hours at ambient temperature. The reaction mixture was diluted with water and was extracted with CH2Cl2. The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Purification of the residue via column chromatography (SiO2, heptane:ethyl acetate 0~65%) gave the title (200 mg, 1.22 mmol, 35% yield). 1H NMR (500 MHz, DMSO-d6) delta ppm 9.00 - 8.93 (m, 1H), 8.86 (q, J = 1.1 Hz, 1H), 7.17 (t, J = 54.0 Hz, 1H); MS (ESI+) m/z 186 (M+Na)+.
35%	With triethylamine tris(hydrogen fluoride); ethanaminium,N-(difluoro-lambda4-sulfanylidene)-N-ethyl-,tetrafluoroborate; In dichloromethane; at 20℃; for 18h;	To a solution of <strong>[88625-24-5]5-chloropyrazine-2-carbaldehyde</strong> (500 mg, 3.51 mmol) in CH2CI2 (10 mL) was added (diethylamino)difluorosulfonium tetrafluoroborate (2.0 g, 8.77 mmol) and triethylamine trihydrofluoride (0.57 mL, 3.51 mmol). The reaction mixture was stirred for 18 hours at ambient temperature. The reaction mixture was diluted with water and was extracted with CH2CI2. The organic layer was dried over anhydrous MgSO/t, filtered and concentrated under reduced pressure. Purification of the residue via column chromatography (Si(, heptane:ethyl acetate 0-65%) gave the title (200 mg, 1.22 mmol, 35% yield). JH NMR (500 MHz, DMSO- ) delta ppm 9.00 - 8.93 (m, 1H), 8.86 (q, J = 1.1 Hz, 1H), 7.17 (t, J = 54.0 Hz, 1H); MS (ESI+) m/z 186 (M+Na)+.

Reference： [1]Patent: WO2017/193063,2017,A1 .Location in patent: Page/Page column 537
[2]Patent: WO2019/90076,2019,A1 .Location in patent: Page/Page column 463-464

26
[ 88625-24-5 ]
(R)-N-(1-(1H-indol-3-yl)propan-2-yl)-2-fluoro-2-methylpropan-1-amine [ No CAS ]
(1S,3R)-1-(5-chloropyrazin-2-yl)-2-(2-fluoro-2-methylpropyl)-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With acetic acid; In toluene; at 90℃; for 4h;Inert atmosphere;	5-Chloropyrazine-2-carbaldehyde (314 mg, 2.20 mmol) was added to a solution of (R)-Nis (1 -(1 H-indol-3 -yl)propan-2-yl)-2-fluoro-2-methylpropan- 1-amine (33% wt in toluene; 1.7g, 2.2 mmol) in toluene (7.9 mL) and acetic acid (0.9 mL). The reaction was heated to 90C. After 4 hours, the reaction was cooled, the volatiles were evaporated, and the resulting residue was dissolved in EtOAc. This organic layer was washed with saturated aqueous NaHCO3, dried over sodium sulfate, filtered, and concentrated under reduced pressure. Theresulting residue was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in heptane. Product fractions were evaporated to dryness to afford (1S,3R)-1-(5- chloropyrazin-2-yl)-2-(2-fluoro-2-methylpropyl)-3 -methyl-2,3 ,4,9-tetrahydro- 1 Hpyrido[3,4-b]indole (791 mg, 96%) as a beige solid. 1H NMR (500 MHz, CDC13, 27 C) 1.30 (3H, s), 1.33 (3H, d), 1.50 (3H, d), 2.63 (2H, d), 2.70 - 2.85 (2H, m), 3.23 (1H, q),5.30 (1H, s), 7.09 (1H, ddd), 7.17 (1H, ddd), 7.38 (1H, dt), 7.49 (1H, d), 8.48 (1H, s), 8.49 (1H, d), 8.84 - 8.87 (1H, m). mlz: ES+ [M+H]+ 373.

Reference： [1]Patent: WO2018/19793,2018,A1 .Location in patent: Page/Page column 148; 149

27
[ 72788-94-4 ]
[ 88625-24-5 ]

Yield	Reaction Conditions	Operation in experiment
50.7%	With manganese(IV) oxide; In chloroform; for 2h;Reflux;	To a solution of Intermediate 112A (2.00 g, 13.84 mmol) in CHCl3 (20 mL) was added active manganese dioxide (4.81 g, 55.3 mmol) and the resulting suspension was refluxed for 2 h. The reaction mixture was cooled to ambient temperature, filtered through Celite and washed with CHCl3 (200 mL). The combined filtrates were washed with brine (200 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Redisep-24 g, 20-30 % EtOAc/ n-hexane) to obtain Intermediate 112B (1.00 g, 50.70%) as a white solid.1H NMR (400 MHz, DMSO-d6) delta ppm 8.98 (d, J = 1.51 Hz, 1 H), 9.04 (d, J = 1.51 Hz, 1 H), 10.07 (s, 1 H). LCMS: The compound did not ionize well.

Reference： [1]Patent: WO2018/93569,2018,A1 .Location in patent: Page/Page column 196Intermediate 112B: 5-chloropyrazine-2-carbaldeh

28
[ 88625-24-5 ]
[ 6228-47-3 ]
2-(but-1-enyl)-5-chloro-pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%		tert-Butyl (1R,3r,5S)-3-[5-butylpyrazin-2-yl]oxy-8-azabicyclo[3.2.1]octane-8-carboxylate. Step 1. To a solution of n-propyl-triphenylphosphonium bromide (0.745 g, 1.1 eq., 1.94 mmol) in dry THF (168 mL) n-BuLi (2.5M in hexane) (0.785 mL, 1.1 eq., 1.94 mmol) was added dropwise at 0C. and the reaction mixture was stirred at the same temperature for 45 min. 5-Chloropyrazine-2-carbaldehyde (0.745 g, 1.1 eq., 1.94 mmol) was added and the crude mixture stirred at room temperature for 16 h, quenched with water (20 mL) and extracted with EtOAc (230 mL). The organic extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo to furnish a crude product, which was purified by flash chromatography eluting with cyclohexane/EtOAc (9:1) to give (E/Z)-2-(but-1-enyl)-5-chloro-pyrazine (90 mg, 30%), as a 1:2 cis/trans mixture of isomers.

Reference： [1]Patent: US2019/135778,2019,A1 .Location in patent: Paragraph 0172-0173

29
[ 88625-24-5 ]
tert-butyl (1R,3r,5S)-3-[5-[butyl-1-enyl]-pyrazin-2-yl]oxy-8-azabicyclo[3.2.1]octane-8-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/135778,2019,A1

30
[ 88625-24-5 ]
tert-butyl (1R,3r,5S)-3-[5-butylpyrazin-2-yl]oxy-8-azabicyclo[3.2.1]octane-8-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/135778,2019,A1

31
[ 43032-38-8 ]
[ 88625-24-5 ]
ethyl 3-[4-(5-formylpyrazin-2-yl)piperazin-1-yl]propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
138 mg	With potassium carbonate In dimethyl sulfoxide at 90℃; for 2h;	40 Reference Example 40: Ethyl 3-[4-(5-formylpyrazin-2-yl)piperazin-1-yl]propanoate A mixture of ethyl 3-(piperazin-1-yl)propanoate (0.142 mL), 5-chloropyrazine-2-carbaldehyde (100 mg), potassium carbonate (485 mg) and DMSO (3.5 mL) was stirred at 90°C for 2 hours. The reaction mixture was cooled to room temperature, diluted with saturated aq. ammonium chloride, and then extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography to afford the title compound (138 mg).

Reference： [1]Current Patent Assignee: NIPPON SHINYAKU CO LTD - EP3792260, 2021, A1 Location in patent: Paragraph 0389

32
[ 88625-24-5 ]
[ 16726-41-3 ]
[ 109-77-3 ]
[ 2770406-34-1 ]

Yield	Reaction Conditions	Operation in experiment
47%	Stage #1: 5-chloropyrazine-2-carbaldehyde; isopropylhydrazine monohydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Stage #2: With NBS In N,N-dimethyl-formamide at 20℃; for 2.08333h; Stage #3: malononitrile With potassium etoxide In ethanol; N,N-dimethyl-formamide at 80℃; for 2h;	327 5-Amino-3-(5-chloropyrazin-2-yl)-l-isopropyl-pyrazole-4-carbonitrile To a stirred solution of 5-chloropyrazine-2-carbaldehyde (0.30 g, 2.11 mmol) and isopropylhydrazinehydrochloride (0.26 g, 2.32 mmol) in DMF (4 mL) is added DIPEA (0.30 g, 2.32 mmol) in portions at RT under N2. The mixture is stirred for 1 hr at 80 °C then is cooled to RT. To the mixture is added a solution of N-bromosuccinimide (0.41 g, 2.32 mmol) in DMF (4 mL) in portions over 5 min. The mixture is stirred for 2 hr at RT. At the same time, to a stirred solution of malonitrile (0.15 g, 2.32 mmol) in EtOH (2 mL) is added sodium ethoxide (0.39 g, 5.80 mmol) at 0 °C under N2. The mixture is stirred for 30 min at RT. (0366) To the second mixture at 0 °C under N2 is added the first mixture dropwise over 30 min. The reaction is stirred for 2 hr at 80 °C. The mixture is diluted with EtOAc and washed with H2O. The organic layer is concentrated under vacuum. The residue is purified by silica gel chromatography, eluting with a gradient of 3 : 1 to 2: 1 PE:EtOAc to give the title compound (0.26 g, 47%) as a white solid. 1H NMR(d6-DMSO, 300 MHz) 6 (ppm) 8.88 (d, 1H), 8.82 (d, 1H), 6.80 (s, 2H), 4.56 (m, 1H), 1.37 (d, 6H).
47%	Stage #1: 5-chloropyrazine-2-carbaldehyde; isopropylhydrazine monohydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Stage #2: With NBS In N,N-dimethyl-formamide at 20℃; for 2.08333h; Stage #3: malononitrile With potassium etoxide In ethanol; N,N-dimethyl-formamide at 80℃; for 2h;	327 5-Amino-3-(5-chloropyrazin-2-yl)-l-isopropyl-pyrazole-4-carbonitrile To a stirred solution of 5-chloropyrazine-2-carbaldehyde (0.30 g, 2.11 mmol) and isopropylhydrazinehydrochloride (0.26 g, 2.32 mmol) in DMF (4 mL) is added DIPEA (0.30 g, 2.32 mmol) in portions at RT under N2. The mixture is stirred for 1 hr at 80 °C then is cooled to RT. To the mixture is added a solution of N-bromosuccinimide (0.41 g, 2.32 mmol) in DMF (4 mL) in portions over 5 min. The mixture is stirred for 2 hr at RT. At the same time, to a stirred solution of malonitrile (0.15 g, 2.32 mmol) in EtOH (2 mL) is added sodium ethoxide (0.39 g, 5.80 mmol) at 0 °C under N2. The mixture is stirred for 30 min at RT. (0366) To the second mixture at 0 °C under N2 is added the first mixture dropwise over 30 min. The reaction is stirred for 2 hr at 80 °C. The mixture is diluted with EtOAc and washed with H2O. The organic layer is concentrated under vacuum. The residue is purified by silica gel chromatography, eluting with a gradient of 3 : 1 to 2: 1 PE:EtOAc to give the title compound (0.26 g, 47%) as a white solid. 1H NMR(d6-DMSO, 300 MHz) 6 (ppm) 8.88 (d, 1H), 8.82 (d, 1H), 6.80 (s, 2H), 4.56 (m, 1H), 1.37 (d, 6H).

Reference： [1]Current Patent Assignee: ELI LILLY & CO; EVOTEC AG - WO2022/98970, 2022, A1 Location in patent: Page/Page column 135; 136
[2]Current Patent Assignee: ELI LILLY & CO; EVOTEC AG - WO2022/98970, 2022, A1 Location in patent: Page/Page column 135; 136

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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. 88625-24-5 ] {[proInfo.proName]}

Quality Control of [ 88625-24-5 ]

Related Doc. of [ 88625-24-5 ]

Product Details of [ 88625-24-5 ]

Calculated chemistry of [ 88625-24-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 88625-24-5 ]

Application In Synthesis of [ 88625-24-5 ]

[ 88625-24-5 ] Synthesis Path-Upstream 1~4

[ 88625-24-5 ] Synthesis Path-Downstream 1~32

Related Functional Groups of [ 88625-24-5 ]

Chlorides

Aldehydes

Related Parent Nucleus of [ 88625-24-5 ]

Pyrazines

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Prevention

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Storage

Disposal

Physical hazards

Health hazards

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[ 88625-24-5 ]

Related Parent Nucleus of
[ 88625-24-5 ]