1192814-45-1|5,6-Dichloropyridin-2-amine| Ambeed

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Quality Control of [ 1192814-45-1 ] Purity: 98% SDS Specification

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Product Details of [ 1192814-45-1 ]

CAS No. :	1192814-45-1
Formula :	C₅H₄Cl₂N₂
M.W :	163.00
SMILES Code :	NC1=NC(Cl)=C(Cl)C=C1
MDL No. :	MFCD17012012
InChI Key :	LULBBYYBHKFKBH-UHFFFAOYSA-N
Pubchem ID :	53485506

Safety of [ 1192814-45-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1192814-45-1 ]

* 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 [ 1192814-45-1 ]

[ 1192814-45-1 ] Synthesis Path-Downstream 1~35

1
[ 1192814-44-0 ]
[ 1192814-45-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With hydrogenchloride; In ethanol; water; at 85 - 90℃; for 4h;	A mixture of N-(5,6-dichloropyridin-2-yl)pivalamide(790 mg, 3.20 mmol), hydrochloric acid, 37% (1.25ml.), water (1.25 ml.), and EtOH (3 mL) was heated for 4 hrsin an oil bath at 85-90 C. LCMS showed nearly completeconversion to product. The reaction was cooled to room temperatureand the reaction mixture was evaporated down to asmall volume, then transferred to a separatory funnel where it was partitioned between aqueous sodium carbonate and ethylacetate. The layers were separated, the aqueous phase waswashed again with ethyl acetate, and the combined organicphases were washed with brine, dried over MgSO4 , filtered,and evaporated to give a white solid. The material was subjectedto a Biotage colunm in 20% ethyl acetate/hexane,collecting the main component. 5,6-Dichloropyridin-2amine (0.49 g, 2.98 mmol, 93%) was obtained as a white solid.

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1261 - 1273.
[2]Patent: JP5714745,2015,B2 .Location in patent: Paragraph 0470; 0472.
[3]Bioorganic Chemistry,2020,vol. 98.
[4]Molecules,2020,vol. 25.

2
[ 1032528-06-5 ]
[ 1192814-45-1 ]
[ 1357159-28-4 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1261 - 1273.

3
[ 1192814-45-1 ]
[ 1357159-29-5 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1261 - 1273.

4
[ 1192814-45-1 ]
[ 1357159-30-8 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1261 - 1273.

5
[ 86847-84-9 ]
[ 1192814-45-1 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1261 - 1273.
[2]Patent: JP5714745,2015,B2 .
[3]Bioorganic Chemistry,2020,vol. 98.
[4]Molecules,2020,vol. 25.

6
[ 1192814-45-1 ]
tert-butyl (5,6-dichloro-4-iodopyridin-2-yl)carbamate [ No CAS ]

References: [1]Patent: WO2015/107494,2015,A1 .
[2]Patent: WO2015/107495,2015,A1 .
[3]Patent: WO2016/203405,2016,A1 .
[4]Patent: US2017/1975,2017,A1 .
[5]Patent: WO2020/81848,2020,A1 .

7
[ 1192814-45-1 ]
tert-butyl (4-((3-amino-5-chloropyrazin-2-yl)thio)-5,6-dichloropyridin-2-yl)carbamate [ No CAS ]

References: [1]Patent: WO2015/107494,2015,A1 .
[2]Patent: WO2015/107495,2015,A1 .
[3]Patent: US2017/1975,2017,A1 .
[4]Patent: US2017/15680,2017,A1 .

8
[ 1192814-45-1 ]
3-((6-amino-2,3-dichloropyridin-4-yl)thio)-6-chloropyrazin-2-amine dihydrochloride [ No CAS ]

References: [1]Patent: WO2015/107494,2015,A1 .
[2]Patent: US2017/1975,2017,A1 .
[3]Patent: US2017/15680,2017,A1 .

9
[ 24424-99-5 ]
[ 1192814-45-1 ]
tert-butyl (5,6-dichloropyridin-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%		LiHMDS (1M in THF; 26 mL, 26.99 mmol) was added drop wise to a stirred solution of <strong>[1192814-45-1]5,6-dichloropyridin-2-amine</strong> (2.0 g, 12.27 mmol) in THF (64 mL) at 0 C, and the reaction mixture was stirred for 15 minutes at the same temperature. Boc2O (3.1 mL, 13.49 mmol) was added and stirred for 15 minutes at this temperature. The reaction mixture was allowed to warm to room temperature and stirred for another 30 minutes. After completion (monitored by TLC), the reaction mixture was quenched with ice-cooled water (20 mL) and extracted with ethyl acetate (3 X 30 mL). The combined organics were washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate was removed under reduced pressure to get crude, which was purified by silica gel combiflash chromatography using 5% ethyl acetate in hexane as an eluant to afford tert-butyl (5,6-dichloropyridin-2-yl)carbamate (2.8 g, 86%) as a solid. LCMS: 207 (M+H-56).
74%		To a solution of <strong>[1192814-45-1]5,6-dichloropyridin-2-amine</strong> (2.1 g, 12.8 mmol) in anhydrous THF (20 mL) was added NaHMDS (25.6 mL, 25.6 mmol) at 0 C. The reaction mixture was stirred at this temperature for 30 mins, then the solution of (Boc)20 (2.9 g, 13.4 mmol) in anhydrous THF (10 mL) was added. The resulting mixture was stirred at 0 C for 1.5 hours. The mixture was quenched with saturated NH4Cl and extracted with ethyl acetate (50 mL x 2). The organic phases were washed with brine (20 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo to give a residue, which was purified by silica gel chromatography (ethyl acetate in petroleum ether = 0% to 10%) to afford /c/V-butyl (5,6- dichloropyridin-2-yl)carbamate (2.5 g, 74% yield) as a colorless oil.
790 mg		Step a: To a solution of <strong>[1192814-45-1]5,6-dichloropyridin-2-amine</strong> (590 mg, 3.62 mmol) in THF (5 mL) was added LiHMDS (1 M in THF, 7.96 mL, 7.96 mmol) at 0C. The reaction was stirred for 10 min at 0 C then a solution of B0C2O (869 mg, 3.98 mmol) in THF (5 mL) was added to reaction mixture. The resulting solution was stirred for 15 min at 0 C then taken to pH 4 by addition of 1 M HC1. The solution was diluted with EtOAc, washed with sat. aq NaHC03, brine, dried over Na2S04, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica chromatography (0 to 40% gradient of EtO Ac/heptane) to give fer?-butyl (5,6-dichloropyridin-2-yl)carbamate (790 mg, 3.00 mmol). NMR (400 MHz, CHLOROFORM-^ δ ppm 7.86 (d, J=8.7 Hz, 1 H), 7.70 (d, J=8.7 Hz, 1 H), 7.20 (br s, 1 H), 1.51 (s, 9 H). MS m/z 232.9 (M+H-?Bu)+.

790 mg		To a solution of <strong>[1192814-45-1]5,6-dichloropyridin-2-amine</strong> (590 mg, 3.62 mmol) in THF (5 mL) was added LiHMDS (1 M in THF, 7.96 mL, 7.96 mmol) at 0 C. The reaction was stirred for 10 min at 0 C then a solution of B0C2O (869 mg, 3.98 mmol) in THF (5 mL) was added to reaction mixture. The resulting solution was stirred for 15 min at 0 C then taken to pH 4 by addition of 1 M HC1. The solution was diluted with EtOAc, washed with sat. aq NaHCC , brine, dried over Na2S04, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica chromatography (0 to 40% gradient of EtO Ac/heptane) to give fer?-butyl (5,6-dichloropyridin-2-yl)carbamate (790 mg, 3.00 mmol). NMR (400 MHz, CHLOROFORM-^ δ ppm 7.86 (d, J=8.7 Hz, 1 H), 7.70 (d, J=8.7 Hz, 1 H), 7.20 (br s, 1 H), 1.51 (s, 9 H). MS m/z 232.9 (M+H-?Bu)+.
3.12 g		Step a: To a 0 C solution of 5,6-dichloropyridin-2-ammne (2.445 g, 15 mmol) in THF (60 mL) was added LiHMDS (1 M in THF, 33.0 mL, 33.0 mmol) dropwise and the reaction mixture was stirred for 10 mm at 0 C. Boc2O (3.60 g, 16.5 mmol) in THF (20 mL) was added and the resulting mixture was stirred for 15 mm at this temperature. The reaction mixture was allowed to warm to RT and taken to pH 4 using aq. 1 N HC1. The aqueous layer was separated and extracted with EtOAc (2 x 20 mL). The combined organic phases were washed with sat. aq. NaHCO3, dried over Mg504, filtered, and the volatiles were removed under reduced pressure. The residue was purified by silica chromatography (0 to 40% gradient of EtOAc/heptane) to give tert-butyl (5,6-dichloropyridin-2-yl)carbamate (3.12 g, 11.86 mmol). MS m/z 207.8 (M+H-tBu).
3.12 g		Intermediate S-6 6-amino-2 -dichloropyridine-4-thiol Step a: To a 0 C solution of <strong>[1192814-45-1]5,6-dichloropyridin-2-amine</strong> (2.445 g, 15 mmol) in THF (60 mL) was added LiHMDS (1 M in THF, 33.0 mL, 33.0 mmol) dropwise and the reaction mixture was stirred for 10 min at 0 C. B0C2O (3.60 g, 16.5 mmol) in THF (20 mL) was added and the resulting mixture was stirred for 15 min at this temperature. The reaction mixture was allowed to warm to RT and taken to pH 4 using aq. 1 N HC1. The aqueous layer was separated and extracted with EtOAc (2 x 20 mL). The combined organic phases were washed with sat. aq. NaHC(, dried over MgSC , filtered, and the volatiles were removed under reduced pressure. The residue was purified by silica chromatography (0 to 40% gradient of EtOAc/heptane) to give ferf-butyl (5,6-dichloropyridin-2-yl)carbamate (3.12 g, 11.86 mmol). MS m/z 207.8 (M+H-fBu)+.
790 mg		Step a: To a solution of <strong>[1192814-45-1]5,6-dichloropyridin-2-amine</strong> (590 mg, 3.62 mmol) in THF (5 mE) was added EiHMDS (1 M in THF, 7.96 mE, 7.96 mmol) at 0 C. The reaction was stirred for 10 mm at 0 C. then a solution of 13oc20 (869 mg, 3.98 mmol) in THF (5 mE) was added to reaction mixture. The resulting solution was stirred for 15 mm at 0 C. then taken to pH 4 by addition of 1 M HC1. The solution was diluted with EtOAc, washed with sat. aq NaHCO3, brine, dried over Na2504, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica chromatography (0 to 40% gradient ofamine (590 mg, 3.62 mmol) in THF (5 mE) was added EiHMDS (1 M in THF, 7.96 mE, 7.96 mmol) at 0 C. The reaction was stirred for 10 mm at 0 C. then a solution of 13oc20 (869 mg, 3.98 mmol) in THF (5 mE) was added to reaction mixture. The resulting solution was stirred for 15 mm at 0 C. then taken to pH 4 by addition of 1 M HC1. The solution was diluted with EtOAc, washed with sat. aq NaHCO3, brine, dried over Na2504, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica chromatography (0 to 40% gradient of
790 mg		To a solution of 5,6-dichioropyridin-2- amine (590 mg, 3.62 mmol) in THF (5 mE) was added EiHMDS (1 M in THF, 7.96 mE, 7.96 mmol) at 00 C. The reaction was stirred for 10 mm at 00 C. then a solution of 13oc20 (869 mg, 3.98 mmol) in THF (5 mE) was added to reaction mixture. The resulting solution was stirred for 15 mm at 00 C. then taken to pH 4 by addition of 1 M HC1. The solution was diluted with EtOAc, washed with sat. aq NaHCO3, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica chromatography (0 to 40% gradient of EtOAc/heptane) to give tert-butyl (5,6-dichloropyridin-2-yl) carbamate (790 mg, 3.00 mmol). ‘H NMR (400 MHz, CHEOROFORM-d) ö ppm 7.86 (d, J=8.7 Hz, 1H), 7.70 (d, J=8.7 Hz, 1H), 7.20 (br s, 1H), 1.51 (s, 9H). MS mlz 232.9 (M+H-t13u).

References: [1]Patent: WO2020/81848,2020,A1 .Location in patent: Paragraph 00250.
[2]Patent: WO2019/183367,2019,A1 .Location in patent: Paragraph 0237.
[3]Patent: WO2015/107494,2015,A1 .Location in patent: Paragraph 00292.
[4]Patent: WO2015/107495,2015,A1 .Location in patent: Paragraph 00351.
[5]Patent: WO2016/203405,2016,A1 .Location in patent: Paragraph 00265.
[6]Patent: WO2016/203406,2016,A1 .Location in patent: Paragraph 00253.
[7]Patent: US2017/1975,2017,A1 .Location in patent: Paragraph 0328; 0329.
[8]Patent: US2017/15680,2017,A1 .Location in patent: Paragraph 0409; 0410.

10
[ 45644-21-1 ]
[ 1192814-45-1 ]

Yield	Reaction Conditions	Operation in experiment
66%	With N-chloro-succinimide; In acetonitrile; at 80℃; for 18h;	A mixture of 6-chloropyridin-2-amine (2.5 g, 19.4 mmol) and NCS (2.8 g, 21.3 mmol) in MeCN (40 mL) was stirred at 80 C for 18 hours. The reaction mixture was concentrated in vacuo to give a residue, which was purified by silica gel chromatography (ethyl acetate in petroleum ether = 0% to 30%) to afford 5,6-dichloropyridin-2-amine (2.1 g, 66% yield) as a white solid. LCMS m/z [M+H]+ = 162.8.
63%	With N-chloro-succinimide; In acetonitrile; at 80℃; for 18h;	Step 3: 5,6-dichloropyridin-2-amine To a solution of 6-chloropyridin-2-amine (5 g, 38.9 mmol) in acetonitrile (50 ml) was added N- chlorosuccinimide (5.25 g, 39.3 mmol). The reaction was stirred for 18 h at 80 C and then concentrated in vacuo. The residue was purified by chromatography with ethyl acetate/petroleum ether (1/3) to afford 5,6- dichloropyridin-2-amine (4 g, 63%) as a white solid. LCMS (ESI): M+H+ = 163.0. NMR (300 MHz, CDC13) δ 7.42 (d, J = 4.0 Hz, 1H), 6.63 (d, J = 4.0 Hz, 1H), 5.10 (brs, 2H).

References: [1]Patent: WO2019/183367,2019,A1 .Location in patent: Paragraph 0237.
[2]Patent: WO2016/166078,2016,A1 .Location in patent: Page/Page column 28.
[3]ACS Medicinal Chemistry Letters,2016,vol. 8,p. 84 - 89.
[4]Bioorganic Chemistry,2020,vol. 98.
[5]Molecules,2020,vol. 25.

11
[ 638-07-3 ]
[ 1192814-45-1 ]
6,7-dichloro-2-(chloromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With PPA; at 110℃; for 1h;	Step 4: 6,7-Dichloro-2-(chloromethyl)-4H-pyrido[l,2-alpyrimidin-4-one: A mixture of <strong>[1192814-45-1]5,6-dichloropyridin-2-amine</strong> (4 g, 24.5 mmol), ethyl 4-chloro-3-oxobutanoate (8.1 g, 49.2 mmol) and PPA (21 g, 182 mmol) was stirred for 1 h at 110 C. The reaction was poured into water (50 ml) and the pH value of the solution was adjusted to 7 with sodium hydroxide (1 mol/L). The resulting solution was extracted with dichloromethane (3x200 ml) and then concentrated in vacuo. The residue was purified by chromatography with ethyl acetate/petroleum ether (1/3) to afford 6,7-dichloro-2-(chloromethyl)- 4H-pyrido[l,2-a]pyrimidin-4-one (2 g, 31%) as a brown solid. LCMS (ESI): M+H+ = 263.0. NMR (300 MHz, CDCI3) δ 7.58 (d, J = 4.8 Hz, 1H), 7.37 (d, J = 4.8 Hz, 1H), 6.57 (s, 1H), 4.45 (s, 2H).

References: [1]Patent: WO2016/166078,2016,A1 .Location in patent: Page/Page column 28.
[2]ACS Medicinal Chemistry Letters,2016,vol. 8,p. 84 - 89.

12
[ 1192814-45-1 ]
6,7-dichloro-2-[[5-chloro-3-(trifluoromethyl)-1H-pyrazol-1-yl]methyl]-4H-pyrido[1,2-a]pyrimidin-4-one [ No CAS ]

References: [1]Patent: WO2016/166078,2016,A1 .

13
[ 1192814-45-1 ]
(1R,2R)-2-(7-chloro-2-[[5-chloro-3-(trifluoromethyl)-1H-pyrazol-1-yl]methyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-6-yl)cyclopropane-1-carbonitrile [ No CAS ]
(1S,2S)-2-(7-chloro-2-[[5-chloro-3-(trifluoromethyl)-1H-pyrazol-1-yl]methyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-6-yl)cyclopropane-1-carbonitrile [ No CAS ]

References: [1]Patent: WO2016/166078,2016,A1 .

14
[ 1192814-45-1 ]
2-(7-chloro-2-[[5-chloro-3-(trifluoromethyl)-1H-pyrazol-1-yl]methyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-6-yl)cyclopropane-1-carbonitrile [ No CAS ]

References: [1]Patent: WO2016/166078,2016,A1 .

15
[ 1192814-45-1 ]
methyl 3-((6-((tert-butoxycarbonyl)amino)-2,3-dichloropyridin-4-yl)thio)propanoate [ No CAS ]

References: [1]Patent: WO2016/203406,2016,A1 .
[2]Patent: WO2016/203405,2016,A1 .
[3]Patent: WO2020/81848,2020,A1 .

16
[ 1192814-45-1 ]
tert-butyl (5,6-dichloro-4-((5-chloropyrazin-2-yl)thio)pyridin-2-yl)carbamate [ No CAS ]

References: [1]Patent: WO2016/203406,2016,A1 .

17
[ 1192814-45-1 ]
5,6-dichloro-4-((5-chloropyrazin-2-yl)thio)pyridin-2-amine hydrochloride [ No CAS ]

References: [1]Patent: WO2016/203406,2016,A1 .

18
[ 1192814-45-1 ]
(1R,2R)-2-(7-chloro-2-[[5-chloro-3-(trifluoromethyl)-1H-pyrazol-1-yl]methyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-6-yl)cyclopropane-1-carbonitrile [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2016,vol. 8,p. 84 - 89.

19
[ 1192814-45-1 ]
[ 102368-13-8 ]
5,6-dichloro-2-isothiocyanatopyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In dichloromethane; at 40℃; for 3h;	To <strong>[1192814-45-1]5,6-dichloropyridin-2-amine</strong> (0.47 g, 2.88mmol) in dichloromethane (25 mL) was added 1,1'-thiocarbonyldipyridin-2(1H)-one (0.68 g, 2.94 mmol). The reaction was stirred at 40 C. for 3 hours, then cooled to room temperature.The crude material was purified by chromatography(Biotage: 25-100% ethyl acetate/hexane) 2,3-dichloro-6isothiocyanatopyridine(0.48 g, 2.34 mmol, 81% yield) as awhite powder.

References: [1]Patent: JP5714745,2015,B2 .Location in patent: Paragraph 0470; 0473.

20
[ 1192814-45-1 ]
[ 1192811-01-0 ]

References: [1]Patent: JP5714745,2015,B2 .

21
[ 1192814-45-1 ]
tert-butyl (4,5,6-trichloropyridin-2-yl)carbamate [ No CAS ]

References: [1]Patent: WO2019/183367,2019,A1 .

22
[ 1192814-45-1 ]
tert-butyl N-[5,6-dichloro-4-({5-[(3S)-3-[(R)-2-methylpropane-2-sulfinyl]amino}-1,3-dihydrospiro[indene-2,4'-piperidin]-1'-yl]pyrazin-2-yl}sulfanyl)pyridin-2-yl]carbamate [ No CAS ]

References: [1]Patent: WO2019/183367,2019,A1 .

23
[ 1192814-45-1 ]
(S)-1'-(5-((6-amino-2,3-dichloropyridin-4-yl)thio)pyrazin-2-yl)-1,3-dihydrospiro[indene-2,4'-piperidin]-1-amine hydrochloride [ No CAS ]

References: [1]Patent: WO2019/183367,2019,A1 .

24
[ 1192814-45-1 ]
[ 203794-33-6 ]