[ CAS No. 131052-40-9 ]

Name: 131052-40-9|Methyl 5-((tert-butoxycarbonyl)amino)picolinate|98%
Brand: Ambeed
SKU: A1234223
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Quality Control of [ 131052-40-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 131052-40-9 ]

Product Details of [ 131052-40-9 ]

CAS No. :	131052-40-9	MDL No. :	MFCD16036517
Formula :	C₁₂H₁₆N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GPVMPPDFEOSPND-UHFFFAOYSA-N
M.W :	252.27 g/mol	Pubchem ID :	14842342
Synonyms :

Calculated chemistry of [ 131052-40-9 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	6
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	65.76
TPSA :	77.52 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.45
Log Po/w (XLOGP3) :	1.6
Log Po/w (WLOGP) :	2.02
Log Po/w (MLOGP) :	0.76
Log Po/w (SILICOS-IT) :	1.15
Consensus Log Po/w :	1.6

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.26
Solubility :	1.38 mg/ml ; 0.00546 mol/l
Class :	Soluble
Log S (Ali) :	-2.84
Solubility :	0.365 mg/ml ; 0.00145 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.06
Solubility :	0.221 mg/ml ; 0.000875 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.54

Safety of [ 131052-40-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 131052-40-9 ]

* 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 [ 131052-40-9 ]
Downstream synthetic route of [ 131052-40-9 ]

[ 131052-40-9 ] Synthesis Path-Upstream 1~1

1
[ 131052-40-9 ]
[ 323578-38-7 ]

Yield	Reaction Conditions	Operation in experiment
67%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 12 h; Inert atmosphere	Step 3. tert-Butyl (6-(hydroxymethyl)pyridin-3-yl)carbamate. LAH powder (36 g, 0.96 mol) was suspended in dry THF (1000 ml) under N₂atmosphere and cooled to 0° C. To the mixture was added compound 3 (150 g, 0.60 mol) in dry THF (1000 ml) slowly at 0° C. The reaction mixture was gradually warmed to room temperature and stirred for 12 h. TLC (PE/EA, 1:1) showed that the reaction was complete, and the reaction was quenched with dropwise addition of THF-Water (9:1, 400 mL) followed by 90 ml 15percent NaOH aqueous and 50 ml of water at 0° C., stirred for 0.5 h at room temperature, and filtered through a pad of Celite®, and then washed with THF (4×1000 ml). The filtrate was concentrated under reduced pressure to give the crude which was purified by column chromatography over silica gel eluting with PE/EA (2:1-1:2). The desired fraction was concentrated to afford tert-butyl (6-(hydroxymethyl)pyridin-3-yl)carbamate (450 g, 67percent) as a white solid. ¹H NMR (400 MHz, DMSO-d₆) δ 9.58-9.40 (m, 1H), 8.59-8.45 (m, 1H), 7.95-7.78 (m, 1H), 7.42-7.22 (m, 1H), 5.42-5.21 (m, 1H), 4.58-4.40 (m, 2H), 1.48 (s, 9H).
60%	With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 12 h; Inert atmosphere	To a stirred solution of methyl 5-[(tert-butoxy)carbonyl]amino}pyridine-2- carboxylate (EV-AX4571-001, 2.73 g, 10.82 mmol) in THF (60 ml) at 0 °C under an atmosphere of nitrogen was added 4M lithium tetrahydridoaluminate(l-) in diethyl ether (4.1 ml) drop-wise, the reaction was allowed to warm to room temperature and stirred for a further 12h. The reaction was quenched by addition of THF:water (9: 1, 15 ml), followed by 10percent sodium hydroxide (10 ml) and then water (10 ml). The reaction mixture was then filtered through a pad of Kieselguhr, rinsing with THF (3 x 50 ml). The filtrate was concentrated in vacuo and the crude was purified by flash column chromatography (50-100percent) EtOAc/heptane then 0-10percent Methanol/EtOAc) to obtain 1.50 g (60percent) of tert-butyl N-[6- (hydroxymethyl)pyridin-3-yl]carbamate EV-AX4573-001 as an off-white solid. LCMS (method D): retention time 0.70min, M/z = 224 (M + 1).

Reference： [1] European Journal of Inorganic Chemistry, 2010, # 13, p. 1913 - 1928
[2] Patent: US2015/158864, 2015, A1, . Location in patent: Paragraph 0295
[3] Patent: WO2017/100594, 2017, A1, . Location in patent: Paragraph 00304
[4] Patent: WO2006/51270, 2006, A1, . Location in patent: Page/Page column 146

[ 131052-40-9 ] Synthesis Path-Downstream 1~50

1
[ 74-83-9 ]
[ 131052-40-9 ]
[ 112888-55-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride 1.) DMF_. 2,) 2h; Multistep reaction;

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

2
[ 74-96-4 ]
[ 131052-40-9 ]
5-(tert-Butoxycarbonyl-ethyl-amino)-pyridine-2-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride 1.) DMF_. 2,) 2h; Multistep reaction;

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

3
[ 762-49-2 ]
[ 131052-40-9 ]
5-[tert-Butoxycarbonyl-(2-fluoro-ethyl)-amino]-pyridine-2-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride 1.) DMF_. 2,) 2h; Multistep reaction;

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

4
[ 17874-76-9 ]
[ 75-65-0 ]
[ 131052-40-9 ]

Yield	Reaction Conditions	Operation in experiment
55%	With diphenylphosphoranyl azide; triethylamine for 3.5h; Heating;
55%	With diphenyl phosphoryl azide; triethylamine Reflux;
	With diphenyl phosphoryl azide; triethylamine for 3.5h; Heating / reflux;	354.B A solution of 6-(methoxycarbonyl)nicotinic acid (1 g, 5.5 mmol), diphenylphosphoryl azide (1.19 mL, 5.5 mmol) and triethylamine (0.77 mL, 5.5 mmol) in tert-butanol (10 mL) was stirred under reflux for 3.5 h. The solvent was evaporated to give a yellow oil which was dissolved in EtOAC (140 mL). The solution was washed successively with 5% aqueous citric acid, H2O, aqueous NaHCO3, brine (30 mL each) and dried over MgSOφ Evaporation of the solvent and trituration with toluene (30 mL) gave the desired product as a pale yellow solid. LCMS calc. = 252.26; found = 253.2 (M+l)+.

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]
[2]Location in patent: scheme or table Ulrich, Sebastien; Petitjean, Anne; Lehn, Jean-Marie [European Journal of Inorganic Chemistry, 2010, # 13, p. 1913 - 1928]
[3]Current Patent Assignee: MERCK & CO INC - WO2007/70173, 2007, A2 Location in patent: Page/Page column 146

5
[ 131052-40-9 ]
[ 106-95-6 ]
5-(Allyl-tert-butoxycarbonyl-amino)-pyridine-2-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride 1.) DMF_. 2,) 2h; Multistep reaction;

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

6
[ 131052-40-9 ]
[ 106-96-7 ]
[ 112888-59-2 ]

Yield	Reaction Conditions	Operation in experiment
90%		4 EXAMPLE 4 Chem., 1980, 23, 1405, methyl 5-(N-tert-butoxycarbonylamino)pyridine-2-carboxylate was reacted with prop-2-ynyl bromide to give methyl 5-[N-tert-butoxycarbonyl-N-(prop-2-ynyl)amino]pyridine-2-carboxylate in 90% yield.
	With sodium hydride 1.) DMF, 2.) 2 h; Yield given. Multistep reaction;

Reference： [1]Current Patent Assignee: BOSTON SCIENTIFIC CORP - US5089499, 1992, A
[2]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

7
[ 131052-40-9 ]
[ 112888-56-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h
	Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: lithium hydroxide monohydrate / water; methanol / 20 °C

8
[ 131052-40-9 ]
[ 112888-57-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

9
[ 131052-40-9 ]
Allyl-(6-chlorocarbonyl-pyridin-3-yl)-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

10
[ 131052-40-9 ]
5-(Allyl-tert-butoxycarbonyl-amino)-pyridine-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

11
[ 131052-40-9 ]
5-(tert-Butoxycarbonyl-ethyl-amino)-pyridine-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

12
[ 131052-40-9 ]
(6-Chlorocarbonyl-pyridin-3-yl)-ethyl-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

13
[ 131052-40-9 ]
(6-Chlorocarbonyl-pyridin-3-yl)-prop-2-ynyl-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) NaH / 1.) DMF, 2.) 2 h 2: 84 percent / 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

14
[ 131052-40-9 ]
[ 132463-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF, 2.) 2 h 2: 84 percent / 1 N aq. NaOH / aq. ethanol / 16 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

15
[ 131052-40-9 ]
5-[tert-Butoxycarbonyl-(2-fluoro-ethyl)-amino]-pyridine-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

16
[ 131052-40-9 ]
(6-Chlorocarbonyl-pyridin-3-yl)-(2-fluoro-ethyl)-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

17
[ 131052-40-9 ]
[ 132462-95-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h 4: Et₃N / CH₂Cl₂ / 16 h 5: 64 percent / CF₃COOH / 0.5 h / 0 °C

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

18
[ 131052-40-9 ]
[ 132462-96-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h 4: Et₃N / CH₂Cl₂ / 16 h 5: 67 percent / CF₃COOH / 0.5 h / 0 °C

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

19
[ 131052-40-9 ]
[ 132462-97-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h 4: Et₃N / CH₂Cl₂ / 16 h 5: 67 percent / CF₃COOH / 0.5 h / 0 °C

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

20
[ 131052-40-9 ]
[ 112888-58-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h 4: Et₃N / CH₂Cl₂ / 16 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

21
[ 131052-40-9 ]
[ 132463-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h 4: Et₃N / CH₂Cl₂ / 16 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

22
[ 131052-40-9 ]
[ 132463-48-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h 4: Et₃N / CH₂Cl₂ / 16 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

23
[ 131052-40-9 ]
[ 132463-46-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) NaH / 1.) DMF, 2.) 2 h 2: 84 percent / 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h 4: Et₃N / CH₂Cl₂ / 16 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

24
[ 131052-40-9 ]
[ 132463-49-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h 4: Et₃N / CH₂Cl₂ / 16 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

25
[ 131052-40-9 ]
[ 132462-73-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h 4: Et₃N / CH₂Cl₂ / 16 h 5: 64 percent / CF₃COOH / 0.5 h / 0 °C 6: 45 percent / CaCO₃ / dimethylformamide / 2.5 h / 75 °C 7: 74 percent / 1 N aq. NaOH / ethanol / 4 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

26
[ 131052-40-9 ]
[ 132462-74-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h 4: Et₃N / CH₂Cl₂ / 16 h 5: 67 percent / CF₃COOH / 0.5 h / 0 °C 6: 38 percent / 2,6-lutidine / N,N-dimethyl-acetamide / 5 h / 100 °C 7: 86 percent / 1 N aq. NaOH / ethanol / 4 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

27
[ 131052-40-9 ]
[ 132462-75-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h 4: Et₃N / CH₂Cl₂ / 16 h 5: 67 percent / CF₃COOH / 0.5 h / 0 °C 6: 61 percent / 2,6-lutidine / N,N-dimethyl-acetamide / 5 h / 100 °C 7: 79 percent / 1 N aq. NaOH / ethanol / 4 h

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

28
[ 131052-40-9 ]
[ 132463-17-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h 4: Et₃N / CH₂Cl₂ / 16 h 5: 64 percent / CF₃COOH / 0.5 h / 0 °C 6: 45 percent / CaCO₃ / dimethylformamide / 2.5 h / 75 °C

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

29
[ 131052-40-9 ]
[ 132463-18-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h 4: Et₃N / CH₂Cl₂ / 16 h 5: 67 percent / CF₃COOH / 0.5 h / 0 °C 6: 38 percent / 2,6-lutidine / N,N-dimethyl-acetamide / 5 h / 100 °C

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

30
[ 131052-40-9 ]
[ 132463-19-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h 4: Et₃N / CH₂Cl₂ / 16 h 5: 67 percent / CF₃COOH / 0.5 h / 0 °C 6: 61 percent / 2,6-lutidine / N,N-dimethyl-acetamide / 5 h / 100 °C

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

31
[ 131052-40-9 ]
[ 132462-94-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 1.) NaH / 1.) DMF_. 2,) 2h 2: 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h 4: Et₃N / CH₂Cl₂ / 16 h 5: 100 percent / 0.5 h / 0 °C

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

32
[ 131052-40-9 ]
[ 132462-93-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 1.) NaH / 1.) DMF, 2.) 2 h 2: 84 percent / 1 N aq. NaOH / aq. ethanol / 16 h 3: Et₃N, oxalyl chloride / CH₂Cl₂ / 0.5 h 4: Et₃N / CH₂Cl₂ / 16 h 5: 100 percent / 0.5 h / 0 °C

Reference： [1]Marsham, Peter R.; Hughes, Leslie R.; Jackman, Ann L.; Hayter, Anthony J.; Oldfield, John; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605]

33
[ 157701-59-2 ]
[ 131052-40-9 ]
[ 157701-45-6 ]
methyl 5-[N-(tert-butoxycarbonyl)-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxy-methyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]pyridine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In hexane; 2,4-dichlorophenoxyacetic acid dimethylamine; mineral oil	12 EXAMPLE 12 The 5-[N-methyl-N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]pyridine-2-carboxylic acid used as a starting material was obtained as follows: A solution of methyl 5-[N-(tert-butoxycarbonyl)amino]-pyridine-2-carboxylate (J. Med. Chem., 1991, 1594; 0.32 g) in DMA (10 ml) was added dropwise to a stirred suspension of sodium hydride ›60% dispersion in mineral oil, 0.051 g, from which the oil was removed using hexane! in DMA (5 ml). The mixture was stirred at ambient temperature for 30 minutes. This mixture was added dropwise to a stirred solution of 6-bromo-2-methyl-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4-one (0.5 g) in DMA (10 ml) which had been cooled to -10° C. The resultant mixture was stirred at ambient temperature for 18 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated. The residue was purified by column chromatography using increasingly polar mixtures of hexane and ethyl acetate to give methyl 5-[N-(tert-butoxycarbonyl)-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]pyridine-2-carboxylate as a gum (0.3 g).

Reference： [1]Current Patent Assignee: BOSTON SCIENTIFIC CORP - US5789417, 1998, A

34
[ 131052-40-9 ]
[ 323578-38-7 ]

Yield	Reaction Conditions	Operation in experiment
67%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 12h;Inert atmosphere;	Step 3. tert-Butyl (6-(hydroxymethyl)pyridin-3-yl)carbamate. LAH powder (36 g, 0.96 mol) was suspended in dry THF (1000 ml) under N2 atmosphere and cooled to 0 C. To the mixture was added compound 3 (150 g, 0.60 mol) in dry THF (1000 ml) slowly at 0 C. The reaction mixture was gradually warmed to room temperature and stirred for 12 h. TLC (PE/EA, 1:1) showed that the reaction was complete, and the reaction was quenched with dropwise addition of THF-Water (9:1, 400 mL) followed by 90 ml 15% NaOH aqueous and 50 ml of water at 0 C., stirred for 0.5 h at room temperature, and filtered through a pad of Celite, and then washed with THF (4×1000 ml). The filtrate was concentrated under reduced pressure to give the crude which was purified by column chromatography over silica gel eluting with PE/EA (2:1-1:2). The desired fraction was concentrated to afford tert-butyl (6-(hydroxymethyl)pyridin-3-yl)carbamate (450 g, 67%) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 9.58-9.40 (m, 1H), 8.59-8.45 (m, 1H), 7.95-7.78 (m, 1H), 7.42-7.22 (m, 1H), 5.42-5.21 (m, 1H), 4.58-4.40 (m, 2H), 1.48 (s, 9H).
60%	With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at 0 - 20℃; for 12h;Inert atmosphere;	To a stirred solution of methyl 5-[(tert-butoxy)carbonyl]amino}pyridine-2- carboxylate (EV-AX4571-001, 2.73 g, 10.82 mmol) in THF (60 ml) at 0 C under an atmosphere of nitrogen was added 4M lithium tetrahydridoaluminate(l-) in diethyl ether (4.1 ml) drop-wise, the reaction was allowed to warm to room temperature and stirred for a further 12h. The reaction was quenched by addition of THF:water (9: 1, 15 ml), followed by 10% sodium hydroxide (10 ml) and then water (10 ml). The reaction mixture was then filtered through a pad of Kieselguhr, rinsing with THF (3 x 50 ml). The filtrate was concentrated in vacuo and the crude was purified by flash column chromatography (50-100%) EtOAc/heptane then 0-10% Methanol/EtOAc) to obtain 1.50 g (60%) of tert-butyl N-[6- (hydroxymethyl)pyridin-3-yl]carbamate EV-AX4573-001 as an off-white solid. LCMS (method D): retention time 0.70min, M/z = 224 (M + 1).
		Methyl 5-tert-butoxycarbonylaminopyridine-2-carboxylate (J. Med. Chem., 1991, 34, 1594; 5 g) was dissolved in THF (75 mL) and the mixture was cooled to 00C. Lithium aluminium hydride (IM in THF, 19.8 mL) was added dropwise and the mixture was stirred at room temperature for 1 hour. The mixture was re-cooled to 0C and water (0.75 mL) was carefully added followed in turn by 2Nu aqueous sodium hydroxide solution (0.75 mL) and water (2.25 mL). The resultant mixture was stirred for 30 minutes and filtered. The filtrate was dried over magnesium sulfate and evaporated. There was thus obtained 5-tert-butoxycarbonylamino-2-hydroxymethylpyridine as a solid (2.8 g); 1H NMR Spectrum: (DMSOd6) 1.47 (s, 9H), 4.46 (d, 2H), 5.24 (t, IH), 7.33 (d, IH), 7.84 (m, IH), 8.49 (d, IH), 9.44 (s, IH); Mass Spectrum: M+H+ 225.

Reference： [1]European Journal of Inorganic Chemistry,2010,p. 1913 - 1928
[2]Patent: US2015/158864,2015,A1 .Location in patent: Paragraph 0295
[3]Patent: WO2017/100594,2017,A1 .Location in patent: Paragraph 00304
[4]Patent: WO2006/51270,2006,A1 .Location in patent: Page/Page column 146

35
[ 157701-54-7 ]
[ 131052-40-9 ]
[ 157701-45-6 ]
methyl 5-[N-(tert-butoxycarbonyl)-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxy-methyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]pyridine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In hexane; 2,4-dichlorophenoxyacetic acid dimethylamine; mineral oil	6.1 (1) (1) Methyl 5-[N-(tert-butoxycarbonyl)-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxy-methyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]pyridine-2-carboxylate A solution of methyl 5-[N-(tert-butoxycarbonyl)amino]pyridine-2-carboxylate (J. Med. Chem., 1991, 1594; 0.32 g) in DMA (10 ml) was added dropwise to a stirred suspension of sodium hydride ›60% dispersion in mineral oil, 0.051 g, from which the oil was removed using hexane! in DMA (5 ml). The mixture was stirred at ambient temperature for 30 minutes. This mixture was added dropwise to a stirred solution of 6-bromo-2-methyl-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta-[g]quinazolin-4-one (0.5 g), prepared as described in section 6 of Example 1, in DMA (10 ml) which had been cooled to -10° C. The resultant mixture was stirred at ambient temperature for 18 hours. The mixture was evaporated and the residue was partitioned betwen ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated. The residue was purified by column chromatography using increasingly polar mixtures of hexane and ethyl acetate to give methyl 5-[N-(tert-butoxycarbonyl)-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta-[g]quinazolin-6-yl)amino]pyridine-2-carboxylate as a gum (0.3 g).

Reference： [1]Current Patent Assignee: BOSTON SCIENTIFIC CORP - US5747499, 1998, A

36
[ 131052-40-9 ]
[ 95-85-2 ]
[ 942215-85-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methyl 5-[N-(tert-butoxycarbonyl)amino]-pyridine-2-carboxylate; 2-hydroxy-5-chloro-aniline With PPA at 180℃; for 6h; Stage #2: With sodium hydroxide In water	354.C A suspension of polyphosphoric acid (1 mL), 2-amino-4-chlorophenol (0.114 g, 0.79 mmol) and methyl5-[(tert-butoxycarbonyl)amino]pyridine-2-carboxylate (0.200 g, 0.79 mmol) was heated at 18O0C for 6 h. The reaction mixture was allowed to cool and then poured into H2O (50 mL). The solution was neutralized with 6N NaOH and extracted with EtOAC (3 x 70 mL). The combined organic extracts were washed with brine (50 mL), dried over MgSO4, filtered and concentrated. The crude product was purified by silica gel chromatography (15% MeOH/ CHCl3) to afford 6-(5-chloro-l,3-benzoxazol-2- yl)pyridine-3-amine as a yellow solid. LCMS calc. = 245.66; found = 246.2 (M+l)+.

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2007/70173, 2007, A2 Location in patent: Page/Page column 146

37
[ 24424-99-5 ]
[ 67515-76-8 ]
[ 131052-40-9 ]

Yield	Reaction Conditions	Operation in experiment
93.2%	With sodium hexamethyldisilazane; In N,N-dimethyl-formamide; at -40 - -30℃;	NaHMDS (821.25 ml, 1.643 mol, 2.5 eq) and DMF (400 mL) were added to the reaction flask, and II-22 (100.00 g, 0.657 mol, 1.0 eq) and (Boc)2O (157.61) were added dropwise at -30 to -40C. g, 0.723mol, 1.1eq)DMF (600 mL) solution was added. LC-MS showed that the reaction of the raw material was complete.Tertiary ether (1L) was added at 30-40C, and acetic acid (200.00 g) was added dropwise.Methyl tertiary ether (200 mL) mixed solution was added and stirred for 30 minutes.The reaction solution was poured into a saturated aqueous solution of ammonium chloride (3.5 L) and the layers were separated and separated.The aqueous phase is extracted with methyl tert-butyl ether (1L×2) and the organic phases are combined.Washed (500mL x 3), saturated sodium chloride (500mL x 1),Anhydrous sodium sulfate was dried, and the organic phase was evaporated to remove the solvent and petroleum ether (1L) was added.The slurry was suction filtered and dried to give Compound III-22 as an off-white solid, 154.5 g.Yield: 93.2%.
82.3%	With dmap; In dichloromethane; at 20℃; for 20h;Inert atmosphere;	Methyl 5-aminopicolinate (110 g, 0.723 mol) was dissolved in DCM (2000 ml) at 20 C. under N2. To the reaction mixture, Boc-anhydride (173.6 g, 0.80 mol) and DMAP (8.8 g, 0.0723 mol) were added. The reaction mixture was stirred at 20 C. for 20 h. TLC (PE/EA, 2:1) showed that the starting material was consumed completely. The reaction mixture was filtered and washed with DCM (4×3000 ml). H2O (2000 ml) was added and layers were separated. The organic layer was washed with brine, dried over anhydrous Na2SO4 and evaporated under reduced pressure to give crude product. The crude compound was washed with petroleum ether (4000 mL) and stirred for 1.0 hour. Filtration and evaporation in vacuo afforded methyl 5-((tert-butoxycarbonyl)amino) picolinate (750 g from 550 g of <strong>[67515-76-8]methyl 5-aminopicolinate</strong>, 82.3%) as a white solid for next step without further purification. LC/MS (M+H)=253.1.
60%	With dmap; In dichloromethane; at 20℃; for 5h;Inert atmosphere;	To a stirred solution of <strong>[67515-76-8]methyl 5-aminopyridine-2-carboxylate</strong> (CAS 67515-76-8, 1.8 g, 11.83 mmol) in DCM (40 ml) under an atmosphere of nitrogen was added di-tert-butyl dicarbonate (2.84 g, 13.01 mmol) and N,N-dimethylpyridin-4-amine (0.14 g, 1.18 mmol) and the reaction was stirred at room temperature for 5h. The reaction mixture was filtered (rinsing the filter with DCM), the filtrate was diluted with DCM (100 ml) and washed with water (2 x 100 ml). The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo to obtain 2.73 g (60%) of methyl 5-[(tert-butoxy)carbonyl]amino}pyridine-2-carboxylate EV-AX4571-001 as an off-white solid. LCMS (method D): retention time l .Olmin, M/z = 253 (M + 1).

48%	With dmap; In dichloromethane; at 0 - 20℃;	To a solution of 5-Amino-pyridine-2-carboxylic acid methyl ester (1.0 g, 6.6 mmol) in DCM (15 mL) was added DMAP (8 mg, 0.07 mmol) and (Boc)20 (1.6 g, 7.2 mmol) at ice-bath. The mixture was stirred at RT overnight. Then the reaction mixture was diluted with DCM (20 mL) and washed with water (20 mL). The organic phase was seperated, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (petroleum ether/EtOAc = 2/1) to afford product (0.8 g, 48%) as a white solid. [M+H] MS Calcd.: CI2HI6N20 , 253.1, Found: 253.1.
	With dmap; In dichloromethane; at 20℃; for 20h;	103461 Methyl 5-aminopyridine-2-carboxylate (850 mg, 5.59 mmol), di-tert-hutyl dicarbonate (1.34 g, 6.15 mmol) and 4-dimethylaminopyridine (68 mg, 0.56 mmol) were suspended in dichloromethane (10 mL) and stirred at room temperature for 20 hours. The reaction mixture was concentrated to give a white powder. The powder was suspended in ethyl acetate (20 mL), sonicated, heated to boiling and then filtered. The filtrate was diluted with additional ethyl acetate (20 mL) and loaded onto silica. Purification by FCC (silica, 18- 100% ethyl acetate in heptane) gave the crude title compound 862 mg (51% yield) as a white powder which was used in the next step without further purification. OH NMR (500 MHz, DMSO) 10.01 (s, 1H), 8,71 (d, I = 2.3 Hz, 1H), 8.06 (dd, I = 8.7, 2.4 Hz, 1H), 8.00 (d, I = 8.6 Hz, 111), 3.83 (s, 311), 1.49 (s, 9H). Tr(METCR1278) = 1.64 mi (ESt) (M+H) 253, 83%.

Reference： [1]Patent: CN107602556,2018,A .Location in patent: Paragraph 0115; 0117; 0118
[2]Patent: US2015/158864,2015,A1 .Location in patent: Paragraph 0293
[3]Patent: WO2017/100594,2017,A1 .Location in patent: Paragraph 00302
[4]Patent: WO2020/6497,2020,A1 .Location in patent: Paragraph 00412
[5]Journal of the American Chemical Society,2009,vol. 131,p. 3342 - 3348
[6]Patent: WO2016/33445,2016,A1 .Location in patent: Paragraph 0346

38
[ 131052-40-9 ]
[ 1169827-40-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 3: N,N-dimethyl-formamide / 120 °C / Inert atmosphere 4: Dess-Martin periodane / dichloromethane / 6 h / 20 °C / Inert atmosphere 5: chloroform / 20 °C / Inert atmosphere

Reference： [1]Ulrich, Sebastien; Petitjean, Anne; Lehn, Jean-Marie [European Journal of Inorganic Chemistry, 2010, # 13, p. 1913 - 1928]

39
[ 131052-40-9 ]
[ 1169827-41-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 3: N,N-dimethyl-formamide / 120 °C / Inert atmosphere 4: Dess-Martin periodane / dichloromethane / 6 h / 20 °C / Inert atmosphere 5: chloroform / 48 h / 20 °C / Inert atmosphere

Reference： [1]Ulrich, Sebastien; Petitjean, Anne; Lehn, Jean-Marie [European Journal of Inorganic Chemistry, 2010, # 13, p. 1913 - 1928]

40
[ 131052-40-9 ]
[ 873651-92-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

Reference： [1]Ulrich, Sebastien; Petitjean, Anne; Lehn, Jean-Marie [European Journal of Inorganic Chemistry, 2010, # 13, p. 1913 - 1928]

41
[ 131052-40-9 ]
[ 1246364-58-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 3: N,N-dimethyl-formamide / 120 °C / Inert atmosphere

Reference： [1]Ulrich, Sebastien; Petitjean, Anne; Lehn, Jean-Marie [European Journal of Inorganic Chemistry, 2010, # 13, p. 1913 - 1928]

42
[ 131052-40-9 ]
[ 1246364-59-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 3: N,N-dimethyl-formamide / 120 °C / Inert atmosphere 4: Dess-Martin periodane / dichloromethane / 6 h / 20 °C / Inert atmosphere

Reference： [1]Ulrich, Sebastien; Petitjean, Anne; Lehn, Jean-Marie [European Journal of Inorganic Chemistry, 2010, # 13, p. 1913 - 1928]

43
[ 24242-20-4 ]
[ 131052-40-9 ]

Reference： [1]Patent: US2015/158864,2015,A1
[2]Patent: WO2016/33445,2016,A1

44
[ 131052-40-9 ]
tert-butyl N-[6-(hydroxymethyl)piperidin-3-yl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere 2: acetic acid; platinum(IV) oxide; hydrogen / ethanol / 72 h / 65 °C / 2844.39 Torr / Inert atmosphere
	Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 12 h / 0 - 20 °C / Inert atmosphere 2: platinum(IV) oxide; hydrogen / ethanol / 16 h / 65 °C / 2844.39 Torr / Sealed tube 3: sodium hydrogencarbonate / tetrahydrofuran; water / 4.25 h / 0 - 20 °C 4: 5%-palladium/activated carbon; hydrogen / ethanol / 14 h / 20 °C

Reference： [1]Current Patent Assignee: PFIZER INC - US2015/158864, 2015, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2017/100594, 2017, A1

45
[ 131052-40-9 ]
racemic-benzyl 5-((tert-butoxycarbonyl)amino)-2-(hydroxymethyl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere 2: acetic acid; platinum(IV) oxide; hydrogen / ethanol / 72 h / 65 °C / 2844.39 Torr / Inert atmosphere 3: sodium hydrogencarbonate / tetrahydrofuran; water / 12 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 12 h / 0 - 20 °C / Inert atmosphere 2: platinum(IV) oxide; hydrogen / ethanol / 16 h / 65 °C / 2844.39 Torr / Sealed tube 3: sodium hydrogencarbonate / tetrahydrofuran; water / 4.25 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: PFIZER INC - US2015/158864, 2015, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2017/100594, 2017, A1

46
[ 131052-40-9 ]
(2S,5R)-benzyl 5-((2-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-2-(hydroxymethyl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere 2: acetic acid; platinum(IV) oxide; hydrogen / ethanol / 72 h / 65 °C / 2844.39 Torr / Inert atmosphere 3: sodium hydrogencarbonate / tetrahydrofuran; water / 12 h / 0 - 20 °C 4: N-ethyl-N,N-diisopropylamine / butan-1-ol / 50 °C

Reference： [1]Current Patent Assignee: PFIZER INC - US2015/158864, 2015, A1

47
[ 131052-40-9 ]
[ 74-88-4 ]
[ 112888-55-8 ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: methyl 5-[N-(tert-butoxycarbonyl)amino]-pyridine-2-carboxylate With sodium hydride In N,N-dimethyl-formamide; paraffin oil at 20℃; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; paraffin oil at 20℃;	A10.1 A10.1 : 5-(tert-Butoxycarbonyl-methyl-amino)-pyridine-2-carboxylic acid methyl ester 5-tert-Butoxycarbonylamino-pyridine-2-carboxylic acid methyl ester (282.0 mg; 1.118 mmol) and sodium hydride suspension (60% suspension in paraffin oil; 29.5 mg; 1.230 mmol) were stirred in DMF (3.0 mL) under nitrogen (0346) atmosphere at room temperature for 10 min. lodomethane (174.5 mg; 1.230 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. Further sodium hydride suspension (60% suspension in paraffin oil; 16.1 mg; 0.671 mmol) and iodomethane (95.2 mg; 0.671 mmol) were added and the reaction mixture stirred at room temperature overnight. The mixture was diluted with water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue was dried under high vacuum. Yield: 152.0 mg (51 %) pale-orange solid; (0347) LC/MS (A): Rt: 1.98 min; (M+H) 267.1.
48%	Stage #1: methyl 5-[N-(tert-butoxycarbonyl)amino]-pyridine-2-carboxylate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃;	77.2 Step 2: methyl 5-((tert-butoxycarbonyl)(methyl)amino)picolinate To a solution of methyl 5-((tert-butoxycarbonyl)(methyl)amino)picolinate (700 mg, 0.78 mmol) in DMF (15 mL) was added NaH (200 mg, 60%, 3.33 mmol) at 0 °C, and the mixture was stirred at 0 °C for 30 minutes. Mel was added and the mixture was stirred at rt overnight. The mixture was quenched with water (30 mL) and extracted with EA (30 mL3). The combined organic layers were washed with water (30 mL2) and brine (30 mL), dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (petroleum ether/EtOAc = 2/1) to afford product (150 mg, 48%) as a white solid. [M+H] MS Calcd.: Ci3Hi8N204, 267.1, Found: 267.1.
180 mg	Stage #1: methyl 5-[N-(tert-butoxycarbonyl)amino]-pyridine-2-carboxylate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 18h;	49.3 Step 3, Method 49: Methyl 5-[(tert-butoxy)carbonylj(methyl)amino}pyridine-2- carboxylate 103471 Methyl 5- { [(tert-butoxy)carbonyl] amino}pyridine-2-carboxylate (406 mg, 1.34 mmol) was dissolved in anhydrous N,N-dimethylformamide (5 mL) and cooled to 0 °C. Sodium hydride (60% in mineral oil, 136 mg, 3.34 mmol) was added and the mixture stirred for 15 minutes. lodomethane (100 jiL, 1.60 mrnol) was added and the mixture stirred at room temperature for 18 hours. The reaction mixture was quenched by the addition of water (5 mL) and extracted with ethyl aceate (2 x 15 mL). The combined organic extracts were washed with brine (3 x 10 mL), dried over magnesium sulfate, filtered and concentrated. Purification by FCC (silica, eluent: 50-75% ethyl acetate in heptane) gave the title compound 180 mg (51% yield) as a yellow oil. On NMR (500 MHz, DMSO) 8.70 (d, I = 2.5 Hz, 1H),8.03 (d, I = 8.5 Hz, 1H), 7.91 (dd, .1 = 8.5, 2.6 Hz, 1H), 3.87 (s, 3H), 3.27 (s, 311), 1.43 (s, 9H). Tr(METCR1278) = 1.68 mi (ESj (M+H) 267.

Reference： [1]Current Patent Assignee: MERCK KGAA - WO2020/114892, 2020, A1 Location in patent: Page/Page column 46
[2]Current Patent Assignee: KINNATE BIOPHARMA INC - WO2020/6497, 2020, A1 Location in patent: Paragraph 00412-00413
[3]Current Patent Assignee: CHDI FOUNDATION - WO2016/33445, 2016, A1 Location in patent: Paragraph 0347

48
[ 131052-40-9 ]
C₁₂H₂₂N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen In methanol at 50℃; for 48h; Autoclave;	7 Compound III-22 Preparation of Compound IV-22 Compound III-22 (154.5 g, 0.612 mol, 1.0e.q.) was dissolved in methanol (1L)Place in an autoclave and addHydroquinone palladium carbon(20g) After hydrogen replacement 3 times,After reacting for 2 days at 50°C and 3MPa, the reaction was completed by LC-MS.The ruthenium-palladium carbon was removed by filtration, and the mother liquor was concentrated to obtain compound IV-22 as a light yellow oil, 158.2 g, yield: 100%.

Reference： [1]Current Patent Assignee: PHARMABLOCK SCIENCES (NANJING), INC. - CN107602556, 2018, A Location in patent: Paragraph 0115; 0119; 0120

49
[ 131052-40-9 ]
C₁₇H₂₃N₃O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: hydrogen; / methanol / 48 h / 50 °C / 22502.3 Torr / Autoclave 2: triethylamine / dichloromethane / 2 h / 10 °C 3: sodium tetrahydroborate / tetrahydrofuran / 0.5 h / -30 °C 4: phosphorus tribromide / dichloromethane / 3 h / 0 °C / Reflux 5: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 95 °C
	Multi-step reaction with 5 steps 1: hydrogen; / methanol / 48 h / 50 °C / 22502.3 Torr / Autoclave 2: triethylamine / dichloromethane / 2 h / 10 °C 3: sodium tetrahydroborate / tetrahydrofuran / 0.5 h / -30 °C 4: triphenylphosphine; iodine / 1,4-dioxane / 1 h / -15 - 80 °C 5: sodium hexamethyldisilazane / tetrahydrofuran / 5 h / -30 - 20 °C

Reference： [1]Current Patent Assignee: PHARMABLOCK SCIENCES (NANJING), INC. - CN107602556, 2018, A
[2]Current Patent Assignee: PHARMABLOCK SCIENCES (NANJING), INC. - CN107602556, 2018, A

50
[ 131052-40-9 ]
[ 74-89-5 ]
tert-butyl N-[6-(methylcarbamoyl)-3-pyridyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In methanol at 80℃; for 3h;	2 tert-Butyl N-[6-(methylcarbamoyl)-3-pyridyl]carbamate Methyl 5-(tert-butoxycarbonylamino)pyridine-2-carboxylate (CAS Registry Number: 131052-40-9, WO2016033445) (0.9 g, 3.6 mmol) was dissolved in a 40% methylamine-methanol solution (about 9.8 mol/L) (30 mL, 290 mmol) and the mixture was stirred at 80° C. for 3 hours.After the reaction temperature had returned to room temperature, the solid obtained by concentration under reduced pressure was washed with a mixture solvent of ethyl acetate and hexane to obtain the title compound (600 mg (yield: 70%)) as a white solid.

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - US2020/347030, 2020, A1 Location in patent: Paragraph 0586-0587

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[ CAS No. 131052-40-9 ]

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[ 131052-40-9 ] Synthesis Path-Upstream 1~1

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