[ CAS No. 407623-72-7 ]

Name: 407623-72-7|tert-Butyl (3-(hydroxymethyl)pyridin-4-yl)carbamate|95%
Brand: Ambeed
SKU: A305831
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Quality Control of [ 407623-72-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 407623-72-7 ]

Product Details of [ 407623-72-7 ]

CAS No. :	407623-72-7	MDL No. :	MFCD04035600
Formula :	C₁₁H₁₆N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FNGDRRWCPLWUDZ-UHFFFAOYSA-N
M.W :	224.26	Pubchem ID :	29920835
Synonyms :

Calculated chemistry of [ 407623-72-7 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.45
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	60.61
TPSA :	71.45 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) :	-6.9 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.99
Log Po/w (XLOGP3) :	1.08
Log Po/w (WLOGP) :	1.58
Log Po/w (MLOGP) :	0.3
Log Po/w (SILICOS-IT) :	1.04
Consensus Log Po/w :	1.2

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.86
Solubility :	3.11 mg/ml ; 0.0139 mol/l
Class :	Very soluble
Log S (Ali) :	-2.17
Solubility :	1.51 mg/ml ; 0.00672 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.81
Solubility :	0.344 mg/ml ; 0.00153 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.25

Safety of [ 407623-72-7 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 407623-72-7 ]

* 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 [ 407623-72-7 ]

[ 407623-72-7 ] Synthesis Path-Downstream 1~14

1
[ 407623-72-7 ]
[ 1057650-85-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; Cooling with ice;	5.1.30. tert-Butyl [3-(azidomethyl)pyridin-4-yl]carbamate (2J) Compound 15A (382 mg, 1.70 mmol) was dissolved in THF (5 mL). To this solution were added diphenylphospholyl azide (732 μL, 3.41 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (509 μL, 3.41 mmol) under ice cooling. After stirring at room temperature overnight, the solvent was distilled off in vacuo. The residue was partitioned between AcOEt (50 mL) and water (50 mL). Organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (3% MeOH-CH2Cl2) to obtain the title compound (333 mg, 1.33 mmol, 79%) as a white solid. 1H NMR (CDCl3) δ: 1.55 (9H, s), 4.36 (2H, s), 8.11 (1H, d, J = 5.6 Hz), 8.36 (1H, s), 8.50 (1H, d, J = 5.6 Hz). ESI-MS m/z: 250 (M+H)+.

Reference： [1]Location in patent: experimental part Mochizuki, Akiyoshi; Nagata, Tsutomu; Kanno, Hideyuki; Suzuki, Makoto; Ohta, Toshiharu [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 5, p. 1623 - 1642]

2
[ 407623-72-7 ]
[ 1057650-87-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C / Cooling with ice 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2 h

Reference： [1]Mochizuki, Akiyoshi; Nagata, Tsutomu; Kanno, Hideyuki; Suzuki, Makoto; Ohta, Toshiharu [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 5, p. 1623 - 1642]

3
[ 407623-72-7 ]
[ 1057650-86-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C / Cooling with ice 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2 h 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1 h / 20 °C

Reference： [1]Mochizuki, Akiyoshi; Nagata, Tsutomu; Kanno, Hideyuki; Suzuki, Makoto; Ohta, Toshiharu [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 5, p. 1623 - 1642]

4
[ 116026-93-8 ]
[ 407623-72-7 ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium tetrahydroborate; In methanol; at 20℃; for 1h;	tert-Butyl (3-formylpyridin-4-yl)carbamate12 M.C. Venuti, R.A. Stephenson, R. Alvarez, J.J. Bruno and A.M. Strosberg, J. Med. Chem. 31 (1988), p. 2136. Full Text via CrossRef \| View Record in Scopus \| Cited By in Scopus (60)12 was dissolved in MeOH (10 mL), and NaBH4 (205 mg, 5.43 mmol) was added. After the mixture was stirred at room temperature for 1 h, the solvent was distilled off in vacuo. The residue was partitioned between CH2Cl2 (50 mL) and brine (50 mL). Organic phase was dried over Na2SO4 and concentrated in vacuo. Obtained solid was washed with hexane to obtain the title compound (382 mg, 1.70 mmol, 63%) as a white solid. 1H NMR (CDCl3) delta: 1.53 (9H, s), 4.66 (2H, s), 7.93 (1H, s), 8.08 (1H, d, J = 5.9 Hz), 8.28 (1H, d, J = 5.9 Hz), 8.32 (1H, s). ESI-MS m/z: 225 (M+H)+.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 1623 - 1642

5
[ 24424-99-5 ]
[ 138116-34-4 ]
[ 407623-72-7 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 20℃; for 1.0h;	To a solution of 4-aminopyridme-3-methanol (3) (Alfa Aesar) (806 mg. 6.5 mmol) in ( I LCh (10 mL) a solution of di-tert-butyl-dicarbonate (1.43 g, 6.56 mmol) in Ci hC 'h (5 mL) was added and stirred at room temperature for 1 h (TLC), After 1 h, the solution was acidified with 1 N HQ (7.4 mL, 7.4 mmol). The phases were separated and the aqueous phase was washed with CH2CI2. The aqueous layer was mixed with a fresh portion of CH2CI2 (10 mL) and treated with K2CO3 (71 1 mg, 5.1 mmol). The phases were separated and treated with additional amounts of CH2G2.. The combined organic extracts were dried (MgS04) and evaporated in vacuo to give a 60:40 mixture containing desired product 8 and the O-linked carbonate. Attempts to purify the N-carbamate by flash chromatography from the O- carbonate were unsuccessful due interconversion between these two species in solution at room temperature. -N ViR (CDC13, 500 MHz) delta: 1.53 (91 L s), 4.67 (2H, s), 4.83 (2H, br s), 7.95 ( i i . s), 8.07 (1H, d, ./ 5.5 Hz), 8.28 (I H, d, J ------ 5.5 Hz), 8.48 (1 H, s). This product has been previously synthesized through a different route (Mochizuki, et al, 2011).

Reference： [1]Patent: WO2013/173746,2013,A2 .Location in patent: Paragraph 00196

6
[ 407623-72-7 ]
tert-butyl N-[3-(fluoromethyl)pyridin-4-yl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
113 mg	With triethylamine; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate In dichloromethane at 0℃; for 0.25h;	9 EXAMPLE 9, METHODS [00197] Synthesis of tert-biityl N-[3-(fluoromethyi)pyridln-4-yi]carbamate (9): To a solution of triethylamine (450 μ, 2.76 mmol) in CH2CI2 (5 mL) at - 78 °C was added XtalFluor-E" (473 mg, 207 mmol) and the product from the previous reaction (310 mg, 1 ,38 mmol in 5 mL CH2CI2). The reaction was stirred at 0 °C for 15 min (TLC). Subsequently, the reaction mixture was washed with NaHCQ3 (10 mL) and brine (10 mL). The organic phase was dried (MgS04) and concentrated in vacuo. The crude product was purified by flash chromatography to afford 9 (1 13 mg, 36 % yield). /? ·= 0.5 (1 :3 , hexan.es: EtOAc). 1H-NMR (CDCI3, 500 MHz) δ ppm: 1.56 (9H, s), 5.48 (2H, d, J= 48 Hz), 7.12 (1H, br s), 8.12 (1H, d, J ------- 5.5 Hz), 8.38 (1H, d, J= 3 Hz), 8.32 (I H, s), 8.53 (1H, dd, J2 ;;; 5.5 Hz, J< = 1.0 Hz). 13C- NMR (CDCI3, 125 MHz) δ: 28.2, 80.6, 82.0 (d, J = 15.5 Hz), 1 13.2, 1 18.0 (d, J = 15.5 Hz), 145.6, 150.1, 149.7, 151.7, 152.4. 19F- MR (CDCI3, 470 MHz) δ: -209.3 ft, J = 48 Hz). HR- MS m/z: 227.1 190 ( M } .

Reference： [1]Current Patent Assignee: UNIVERSITY OF CHICAGO - WO2013/173746, 2013, A2 Location in patent: Paragraph 00197

7
C₁₇H₂₄N₂O₆ [ No CAS ]
[ 407623-72-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₁₇H₂₄N₂O₆ With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 23℃; for 2.5h; Inert atmosphere; Stage #2: With Rochelle's salt at -10 - 20℃; Inert atmosphere;