[ CAS No. 89937-26-8 ]

Name: 89937-26-8|1-(6-Chloropyridazin-3-yl)piperidin-4-ol|98%
Brand: Ambeed
SKU: A241523
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Quality Control of [ 89937-26-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 89937-26-8 ]

SDS Specification

Alternatived Products of [ 89937-26-8 ]

Product Details of [ 89937-26-8 ]

CAS No. :	89937-26-8	MDL No. :	MFCD05864736
Formula :	C₉H₁₂ClN₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GYVIZUPSUNWREG-UHFFFAOYSA-N
M.W :	213.66	Pubchem ID :	5200271
Synonyms :

Safety of [ 89937-26-8 ]

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

Application In Synthesis of [ 89937-26-8 ]

* 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.

Upstream synthesis route of [ 89937-26-8 ]
Downstream synthetic route of [ 89937-26-8 ]

[ 89937-26-8 ] Synthesis Path-Upstream 1~1

1
[ 5382-16-1 ]
[ 141-30-0 ]
[ 89937-26-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With triethylamine In dimethyl sulfoxideSealed tube	General procedure: Desired aromatic halide (19 or 32 or 33) (1 equiv), 4-hydroxypiperidine(1 equiv) an aprotic base such as Et3N or K2CO3(2–3 equiv) in DMSO or EtOH was heated in a sealed vessel untilconsumption of the starting material was observed. Work-up consistedof either partial mixture evaporation, addition of water andfiltration of the resulting solid to afford the product (as in case of37) or partition of the partially evaporated mixture between EtOAcand water, extraction of the aqueous layer with portions of EtOAcuntil no UV absorption in the organic extract and then evaporationof the combined organic layer to the crude product that was purifiedvia column chromatography.
89%	With triethylamine In dimethyl sulfoxide at 50℃;	A mixture of 3,6 dichloropyridazine (500 mg, 3.36 mmol), 4-hydroxypiperidine (340 mg, 3.36 mmol) and Et₃N (0.94 mL, 6.72 mmol) in DMSO (5 mL) was stirred at 50 °C overnight. The reaction mixture was then partitioned between EtOAc and water. The water layer was saturated with solid NaCl and extracted with EtOAc portions until no UV absorption was detected in the organic layer. The combined EtOAc layer was then evaporated and the residue was chromato graphed on a silica gel column with 0-100percent EtOAc in hexanes gradient to afford the product, l-(6-chloro-pyridazin-3-yl)-piperidin-4-ol, as a white solid (640 mg, 89percent yield). 1HNMR (600 MHz, CD₃OD) δ 1.54 (m, 2H), 1.94 (m, 2H), 3.28 (m, 2H), 3.89 (apparent sep, J= 4.2 Hz, IH), 4.11 (apparent dt, J= 13.2, 4.8 Hz, 2H), 7.32 (d, J=9.6 Hz, IH), 7.4 (d, J=9.6 Ηζ,ΙΗ). ATR IR (cm^"1) 3199, 3077, 3008, 2991, 2941, 2847, 1583, 1530, 1429, 1362, 1312, 1298, 1257, 1237, 1224, 1184, 1167, 1148, 1107, 1061, 1032, 1012, 981, 921, 835, 766, 745, 670, 634. (ESI) m/z for C₉Hi₂ClN₃0 calculated: 213.07, observed [M+H]:214.

Reference： [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 8, p. 1819 - 1839
[2] Patent: WO2016/54388, 2016, A1, . Location in patent: Page/Page column 57
[3] Journal of Medicinal Chemistry, 1984, vol. 27, # 8, p. 1077 - 1083
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7281 - 7286
[5] Patent: WO2008/46226, 2008, A1, . Location in patent: Page/Page column 42

[ 89937-26-8 ] Synthesis Path-Downstream 1~21

1
[ 5382-16-1 ]
[ 141-30-0 ]
[ 89937-26-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With triethylamine; In dimethyl sulfoxide;Sealed tube;	General procedure: Desired aromatic halide (19 or 32 or 33) (1 equiv), 4-hydroxypiperidine(1 equiv) an aprotic base such as Et3N or K2CO3(2-3 equiv) in DMSO or EtOH was heated in a sealed vessel untilconsumption of the starting material was observed. Work-up consistedof either partial mixture evaporation, addition of water andfiltration of the resulting solid to afford the product (as in case of37) or partition of the partially evaporated mixture between EtOAcand water, extraction of the aqueous layer with portions of EtOAcuntil no UV absorption in the organic extract and then evaporationof the combined organic layer to the crude product that was purifiedvia column chromatography.
89%	With triethylamine; In dimethyl sulfoxide; at 50℃;	A mixture of 3,6 dichloropyridazine (500 mg, 3.36 mmol), 4-hydroxypiperidine (340 mg, 3.36 mmol) and Et3N (0.94 mL, 6.72 mmol) in DMSO (5 mL) was stirred at 50 C overnight. The reaction mixture was then partitioned between EtOAc and water. The water layer was saturated with solid NaCl and extracted with EtOAc portions until no UV absorption was detected in the organic layer. The combined EtOAc layer was then evaporated and the residue was chromato graphed on a silica gel column with 0-100% EtOAc in hexanes gradient to afford the product, l-(6-chloro-pyridazin-3-yl)-piperidin-4-ol, as a white solid (640 mg, 89% yield). 1HNMR (600 MHz, CD3OD) delta 1.54 (m, 2H), 1.94 (m, 2H), 3.28 (m, 2H), 3.89 (apparent sep, J= 4.2 Hz, IH), 4.11 (apparent dt, J= 13.2, 4.8 Hz, 2H), 7.32 (d, J=9.6 Hz, IH), 7.4 (d, J=9.6 Etazeta,IotaEta). ATR IR (cm"1) 3199, 3077, 3008, 2991, 2941, 2847, 1583, 1530, 1429, 1362, 1312, 1298, 1257, 1237, 1224, 1184, 1167, 1148, 1107, 1061, 1032, 1012, 981, 921, 835, 766, 745, 670, 634. (ESI) m/z for C9Hi2ClN30 calculated: 213.07, observed [M+H]:214.
	With hydrogenchloride; In water; at 80℃; for 24.0h;	Into a round-bottom flask equipped with a magnetic stirbar and a reflux condenser was added 3,6-dichloropyridazine (1 equiv.), 4-hydroxypiperidine (1.3 equiv.) and water (200 mL). The suspension was treated with dropwise addition of concentrated hydrochloric acid (1.02 mL, 0.1 equiv.) and the suspension heated to 80 0C for 24 h. The resulting orange solution was cooled to room temperature and basified to pH = 11 with 10 M aqueous sodium hydroxide. The resulting suspension was poured into a separatory funnel containing 1 M aqueous NaOH and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The resulting yellow solid was triturated in ethyl acetate/di ethyl ether and filtered through Whatman No.1 filter paper on a Hirsch funnel to give the title compound as a yellow solid

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 1819 - 1839
[2]Patent: WO2016/54388,2016,A1 .Location in patent: Page/Page column 57
[3]Journal of Medicinal Chemistry,1984,vol. 27,p. 1077 - 1083
[4]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7281 - 7286
[5]Patent: WO2008/46226,2008,A1 .Location in patent: Page/Page column 42

2
[ 3827-49-4 ]
[ 89937-26-8 ]
[ 944808-82-6 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3086 - 3100

3
[ 89937-26-8 ]
[ 944808-17-7 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3086 - 3100

4
[ 89937-26-8 ]
[ 944808-24-6 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3086 - 3100

5
[ 89937-26-8 ]
[ 944808-85-9 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3086 - 3100

6
[ 89937-26-8 ]
[ 944808-88-2 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3086 - 3100

7
[ 89937-26-8 ]
C₁₈H₁₈ClFN₆O [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3086 - 3100

8
[ 916326-10-8 ]
[ 89937-26-8 ]
[ 1020658-45-0 ]

Yield	Reaction Conditions	Operation in experiment
		Into a flame-dried Schlenk flask equipped with a magnetic stirbar and under a N2 atmosphere was added 3-(ethoxycarbonyl)pyridine-5-boronic acid pinacol ester (1 equiv.), l-(6- chloropyridazin-3-yl)piperidin-4-ol (1.1 equiv), Pd2(dba)3 (0.01 equiv.) and tricyclohexylphosphine (0.025 equiv.). The flask was evacuated and back-filled with N2 (repeated 3 times). The solids were suspended in dioxane (0.5 M) and then an aqueous solution of tribasic potassium phosphate (1.7 equiv.) was added. The mixture was heated to 100 C in an oil bath for 3 h. The mixture was cooled, poured into a separatory funnel containing pH 5 buffer and the mixture was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. Purification by column chromatography on silica gel (eluting with 5% MeOH in ethyl acetate) gave the indicated product as a beige solid

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7281 - 7286
[2]Patent: WO2008/46226,2008,A1 .Location in patent: Page/Page column 42; 43

9
C₁₃H₁₉BN₂O₄ [ No CAS ]
[ 89937-26-8 ]
C₁₆H₁₉N₅O₃ [ No CAS ]