[ CAS No. 220364-34-1 ]

Name: 220364-34-1|tert-Butyl 3-(bromomethyl)benzylcarbamate|98%
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Quality Control of [ 220364-34-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 220364-34-1 ]

SDS Specification

Alternatived Products of [ 220364-34-1 ]

Product Details of [ 220364-34-1 ]

CAS No. :	220364-34-1	MDL No. :	MFCD20257493
Formula :	C₁₃H₁₈BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZAWVAHJDHPLCQF-UHFFFAOYSA-N
M.W :	300.19 g/mol	Pubchem ID :	21874548
Synonyms :

Calculated chemistry of [ 220364-34-1 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.46
Num. rotatable bonds :	6
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	72.79
TPSA :	38.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.13
Log Po/w (XLOGP3) :	2.98
Log Po/w (WLOGP) :	3.3
Log Po/w (MLOGP) :	3.05
Log Po/w (SILICOS-IT) :	3.12
Consensus Log Po/w :	3.12

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.44
Solubility :	0.108 mg/ml ; 0.00036 mol/l
Class :	Soluble
Log S (Ali) :	-3.45
Solubility :	0.107 mg/ml ; 0.000356 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.0
Solubility :	0.00301 mg/ml ; 0.00001 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.21

Safety of [ 220364-34-1 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P264-P270-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P362+P364-P405-P501	UN#:	3261
Hazard Statements:	H302+H312-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 220364-34-1 ]

* 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.

Upstream synthesis route of [ 220364-34-1 ]
Downstream synthetic route of [ 220364-34-1 ]

[ 220364-34-1 ] Synthesis Path-Upstream 1~7

1
[ 226070-69-5 ]
[ 220364-34-1 ]

Yield	Reaction Conditions	Operation in experiment
67%	With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃;	The solution of Boc-aminomethylbenzyl alcohol (237 mg), triphenylphosphine (485 mg) and carbon tetrabromide (491 mg) in dichloromethane (10 mL) was stirred at room temperature overnight and then was concentrated. The crude mixture was purified by silica gel chromatography to give the title compound (200 mg; 67percent).
51%	With carbon tetrabromide; triphenylphosphine In tetrahydrofuran for 18 h;	To an ice-cold solution of 3- (hydroxymethylbenzyl) carbamic acid ter-butyl ester (0.7 g, 3.0 mmol) and CBr4 (1.0 g, 3.1 mmol) in THF (14 mL) was added Ph3P (0. 81 g, 3.1 mmol), and the reaction mixture was stirred for 18 h. The reaction mixture was filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, eluent 5: 95 to 15 : 85 EtOAc/hexanes) to afford the 3- (bromomethyl) benzyl- carbamic acid tert-butyl ester as a white solid (0.42 g, 51percent) : I H NMR (300 MHz, MEOD) 8 7.55 (s, 1H), 7.32-7. 27 (m, 2H), 7.21-7. 19 (m, 1H), 4.54 (s, 2H), 4.21 (s, 2H), 1.28 (s, 9H).
51%	With carbon tetrabromide; triphenylphosphine In tetrahydrofuran for 18 h;	To an ice-cold solution of 3- (hydroxymethylbenzyl) carbamic acid ter-butyl ester (0.7 g, 3.0 mmol) and CBr4 (1.0 g, 3.1 mmol) in THF (14 mL) was added Ph3P (0. 81 g, 3.1 mmol), and the reaction mixture was stirred for 18 h. The reaction mixture was filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, eluent 5: 95 to 15 : 85 EtOAc/hexanes) to afford the 3- (bromomethyl) benzyl- carbamic acid tert-butyl ester as a white solid (0.42 g, 51percent) : I H NMR (300 MHz, MEOD) 8 7.55 (s, 1H), 7.32-7. 27 (m, 2H), 7.21-7. 19 (m, 1H), 4.54 (s, 2H), 4.21 (s, 2H), 1.28 (s, 9H).

Reference： [1] Patent: US2006/173183, 2006, A1, . Location in patent: Page/Page column 113
[2] Patent: WO2005/18557, 2005, A2, . Location in patent: Page/Page column 282-283
[3] Patent: WO2005/18557, 2005, A2, . Location in patent: Page/Page column 282-283
[4] Patent: EP1452521, 2004, A1, . Location in patent: Page 55

2
[ 874-97-5 ]
[ 220364-34-1 ]

Reference： [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 19, p. 8140 - 8151
[2] Patent: WO2005/18557, 2005, A2,

3
[ 24964-64-5 ]
[ 220364-34-1 ]

Reference： [1] Patent: WO2005/18557, 2005, A2,

4
[ 28188-41-2 ]
[ 220364-34-1 ]

Reference： [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 19, p. 8140 - 8151

5
[ 391957-11-2 ]
[ 220364-34-1 ]

Reference： [1] Patent: WO2005/18557, 2005, A2,

6
[ 586373-51-5 ]
[ 220364-34-1 ]

Reference： [1] Patent: WO2005/18557, 2005, A2,

7
[ 24424-99-5 ]
[ 34231-22-6 ]
[ 220364-34-1 ]

Reference： [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 19, p. 8140 - 8151

[ 220364-34-1 ] Synthesis Path-Downstream 1~27

1
[ 226070-69-5 ]
[ 220364-34-1 ]

Yield	Reaction Conditions	Operation in experiment
91.2%	With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20℃; for 30h;Inert atmosphere;	tert-butyl (3-(bromomethyl)benzyl)carbamate (2) tert-butyl (3-(hydroxymethyl)benzyl)carbamate (1, AstaTech, 500 mg, 1.0 eq) was dissolved in 8.8 mL anhydrous CH2Cl2 at 0° C. with stirring. CBr4 (838 mg, 1.2 eq) was added spatula-wise over 5 min, followed by PPh3 (663 mg, 1.2 eq) spatula-wise over 10 min. Reaction was left to warm to rt and allowed to stir for 30 hr. CH2Cl2 (50 mL) was added, washed with brine (3*20 mL), evaporated, and purified by column chromatography (hexanes:EtOAc). 2 was afforded as a clear solid (577 mg, 91.2percent), NMR (CDCl3, 400 MHz): delta7.35-7.24 (4H, m), delta 4.88 (1H, br), delta 4.51 (2H, d, J=3.92 Hz), delta 4.34 (2H, d, J=3.60 Hz), delta 1.49 (9H, s).
67%	With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20℃;	The solution of Boc-aminomethylbenzyl alcohol (237 mg), triphenylphosphine (485 mg) and carbon tetrabromide (491 mg) in dichloromethane (10 mL) was stirred at room temperature overnight and then was concentrated. The crude mixture was purified by silica gel chromatography to give the title compound (200 mg; 67%).
51%	With carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; for 18h;	To an ice-cold solution of 3- (hydroxymethylbenzyl) carbamic acid ter-butyl ester (0.7 g, 3.0 mmol) and CBr4 (1.0 g, 3.1 mmol) in THF (14 mL) was added Ph3P (0. 81 g, 3.1 mmol), and the reaction mixture was stirred for 18 h. The reaction mixture was filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, eluent 5: 95 to 15 : 85 EtOAc/hexanes) to afford the 3- (bromomethyl) benzyl- carbamic acid tert-butyl ester as a white solid (0.42 g, 51%) : I H NMR (300 MHz, MEOD) 8 7.55 (s, 1H), 7.32-7. 27 (m, 2H), 7.21-7. 19 (m, 1H), 4.54 (s, 2H), 4.21 (s, 2H), 1.28 (s, 9H).

The title compound was obtained according to the method of Reference Example 21 from t-butyl N-[3-(hydroxymethyl)-benzyl]carbamate.1H-NMR(CDCl3): 1.45 (s, 9H), 4.28 (d, J=6.0Hz, 2H), 4.49 (s, 2H), 5.00 (br, 1H), 7.19-7.22 (m,1H), 7.30-7.36 (m,3H)

Reference： [1]Patent: US2019/144377,2019,A1 .Location in patent: Paragraph 0206
[2]Patent: US2006/173183,2006,A1 .Location in patent: Page/Page column 113
[3]Patent: WO2005/18557,2005,A2 .Location in patent: Page/Page column 282-283
[4]Patent: EP1452521,2004,A1 .Location in patent: Page 55

2
[ 461-72-3 ]
[ 220364-34-1 ]
C₁₆H₂₁N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; at 20℃; for 24h;	The mixture of the title compound from Step A above (90 mg), hydantoin (36 mg), potassium carbonate (150 mg) and tetrabutylammonium iodide (1 mg) in N,N-dimethylformamide was stirred at room temperature for 24 h. The solution was concentrated to dryness, and then dissolved in ethyl acetate (20 mL). The solution was washed with water and brine, dried over magnesium sulfate and concentrated to give the title compound (90 mg) as a yellow solid.

Reference： [1]Patent: US2006/173183,2006,A1 .Location in patent: Page/Page column 113

3
[ 220364-34-1 ]
[ 586373-39-9 ]
[ 586373-50-4 ]

Yield	Reaction Conditions	Operation in experiment
20%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3h;	To a solution of 3-bromo-4- (4- FLUOROBENZYLOXY) pyridine-2 (1H)-ONE (from Step 3, synthesis Example 59) (0.2 g, 0.67 mmol) in DMF (11 ML) was added K2CO3 (0.26 g, 1.3 mmol) and 3- (bromomethyl) benzylcarbamic acid tert-butyl ester (0.23 g, 0. 80 mmol), and the reaction mixture was stirred at 80 °C for 3 hours. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was diluted with a 50percent aqueous solution of brine (24 mL), and extracted with CHC13 (4 x 50 mL). The combined organics was washed water and then brine, dried (MGS04), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 3: 7 EtOAc/hexanes) and recrystallization from MeOH afforded {3- [3-bromo-4- (4- {LUOROBENZYLOXY)-2-OXO-2H-PYRIDIN-L-YLMETHYL] BENZYL} CARBAMIC acid tert-butyl ester as an off-white solid (0.07 g, 20percent): mp 136-138 °C ; LH NMR (300 MHz, CDC13) 8 7.42-7. 37 (m, 2H), 7.30-7. 20 (m, 5H), 7.08 (t, J = 9 Hz, 2H), 6.04 (d, J= 9 Hz, 1H), 5. 16 (s, 2H), 5.14 (s, 2H), 4.28 (d, J = 6 Hz, 1H), 1.44 (s, 9H). ESHRMS M/Z 517.1124 (M+H C2sH27BrFN204 requires 517.1133)

Reference： [1]Patent: WO2005/18557,2005,A2 .Location in patent: Page/Page column 282-284

4
[ 6270-34-4 ]
[ 220364-34-1 ]
[ 4549-74-0 ]
[ 499789-60-5 ]

Yield	Reaction Conditions	Operation in experiment
		0.146 g of lithium was added to 240 ml of liquid ammonia and 60 ml of tetrahydrofuran at -78°C under an atmosphere of nitrogen gas. After stirring for 15 minutes, a solution of 1.297 g of isopropyl furan-2-carboxylate in 60 ml of tetrahydrofuran was added dropwise. After stirring for 15 minutes, 3-methyl-1,3-pentadiene was added drop by drop until the deep blue color faded. To the yellow reaction mixture was added dropwise a solution of 1.246 g of t-butyl N-[3-(bromomethyl)benzyl]carbamate in 60 ml of tetrahydrofuran. After stirring at -78°C for 2 hours, 30 ml of saturated aqueous ammonium chloride was added, and ammonia was evaporated under a flow of nitrogen gas. 200 ml of ethyl acetate and 100 ml of water were added, and the organic layer was washed with 100 ml of brine, dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography, to give 0.921 g of the title compound as a white solid.1H-NMR(CDCl3): 1.12 (t, J=6.3Hz, 3H), 1.14 (t, J=6.3Hz, 3H), 1.44 (s, 9H), 3.07 (d, J=13.6Hz, 1H), 3.21 (d, J=13.6Hz, 1H), 4.27 (br.d, J=5.4Hz, 1H), 4.46 (td, J=1.8, 13.6Hz, 1H), 4.70 (td, J=1.8, 13.6Hz, 1H), 4.79 (br.s, 1H), 5.01 (sept, J=6.3Hz, 1H), 5.82 (td, J=1,8, 6.4Hz, 1H), 5.87 (td, J=1.8, 6.4Hz, 1H), 7.12-7.16 (m, 2H), 7.21 (t, J=7.6Hz, 1H)

Reference： [1]Patent: EP1452521,2004,A1 .Location in patent: Page 55-56

5
[ 220364-34-1 ]
C₂₀H₂₇N₂O₄P [ No CAS ]