[ CAS No. 19989-66-3 ]

Name: 19989-66-3|Benzo[d]thiazol-6-ylmethanol|95%
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Quality Control of [ 19989-66-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 19989-66-3 ]

CAS No. :	19989-66-3	MDL No. :	MFCD04972625
Formula :	C₈H₇NOS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OZGXSRLIKDPNMX-UHFFFAOYSA-N
M.W :	165.21	Pubchem ID :	17860385
Synonyms :

Calculated chemistry of [ 19989-66-3 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	45.75
TPSA :	61.36 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.88
Log Po/w (XLOGP3) :	1.12
Log Po/w (WLOGP) :	1.64
Log Po/w (MLOGP) :	0.91
Log Po/w (SILICOS-IT) :	2.98
Consensus Log Po/w :	1.71

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.11
Solubility :	1.28 mg/ml ; 0.00777 mol/l
Class :	Soluble
Log S (Ali) :	-2.0
Solubility :	1.64 mg/ml ; 0.00995 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.79
Solubility :	0.267 mg/ml ; 0.00162 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 19989-66-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 19989-66-3 ]

* 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 [ 19989-66-3 ]
Downstream synthetic route of [ 19989-66-3 ]

[ 19989-66-3 ] Synthesis Path-Upstream 1~2

1
[ 19989-66-3 ]
[ 19989-67-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With manganese(IV) oxide In dichloromethane at 20℃; for 16 h;	To a mixture of compound B-183 (3.5 g, 21 mmol) in anhydrous dichloromethane (20 mL) was added manganese dioxide (14 g, 0.21 mol) at room temperature. The mixture was stirred at room temperature for 16 hours. On completion, the reaction was filtered, and the filtrate was concentrated in vacuo to give compound B-184 (3.0 g, 88percent yield) as a yellow solid.

Reference： [1] Patent: WO2015/66371, 2015, A1, . Location in patent: Paragraph 00368-00369
[2] Journal of the American Chemical Society, 2008, vol. 130, # 20, p. 6404 - 6410
[3] Journal of Medicinal Chemistry, 1968, vol. 11, # 2, p. 270 - 273

2
[ 19989-66-3 ]
[ 499770-85-3 ]

Yield	Reaction Conditions	Operation in experiment
51%	With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃;	To an ice-cold solution of 71c (607 mg, 3.68 mmol), CBr₄(1.33 g, 4.02 mmol) and DCM (4 mL) was added dropwise a solution of triphenylphosphine (1.05 g, 4.01 mmol) in DCM (4 mL). The resulting solution was gradually warmed to RT and stirred overnight. The crude reaction mixture was concentrated and chromatographed on SiO₂eluting with a EtOAc/hexane gradient (10 to 15percent EtOAc) to afford 430 mg (51percent)of 71d as white solid: ¹H NMR (300 MHz, CDCl₃): 9.02 (s, 1H), 8.10 (d, 1H, J=8.5 Hz), 7.99 (d, 1H, J=1.8 Hz), 7.55 (1H, dd, J=8.5 Hz, 1.8 Hz), 4.65 (s, 2H).

Reference： [1] Patent: US2006/40927, 2006, A1, . Location in patent: Page/Page column 38
[2] Patent: US2005/209274, 2005, A1, . Location in patent: Page/Page column 36

[ 19989-66-3 ] Synthesis Path-Downstream 1~17

1
[ 19989-66-3 ]
[ 19989-67-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With manganese(IV) oxide; In dichloromethane; at 20.0℃; for 16.0h;	To a mixture of compound B-183 (3.5 g, 21 mmol) in anhydrous dichloromethane (20 mL) was added manganese dioxide (14 g, 0.21 mol) at room temperature. The mixture was stirred at room temperature for 16 hours. On completion, the reaction was filtered, and the filtrate was concentrated in vacuo to give compound B-184 (3.0 g, 88% yield) as a yellow solid.

Reference： [1]Patent: WO2015/66371,2015,A1 .Location in patent: Paragraph 00368-00369
[2]Journal of the American Chemical Society,2008,vol. 130,p. 6404 - 6410
[3]Journal of Medicinal Chemistry,1968,vol. 11,p. 270 - 273

2
[ 19989-64-1 ]
[ 19989-66-3 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃;	[0165] The benzothiazole derivative was prepared as shown in Scheme 5. <strong>[19989-64-1]Ethyl benzothiazole-6-carboxylate</strong> 39 was prepared by ring closure of ethyl-4-amino-3-mercaptobenzoate.<xiv> Reduction of this ester under standard conditions at 0 DEG C gave alcohol 40.<xv> Again Mitsunobu coupling of 6-mercaptopurine riboside with 40 gave nucleoside 41 in 56% yield.; [0166] i) LiAlH4/THF, overnight; ii) 6-mercaptopurine riboside, DIPEA, propionitrile, reflux, 18 h.; [0198] To a suspension of 76 mg of LiAlH4 in dry THF (20 mL) under N2 was added dropwise and at 0 DEG C a solution of ester 39 (207 mg, 1 mmol) in dry THF (6.7 ml). After 2 h. the ice bath was removed and the mixture was stirred overnight at rt, then cooled to 0 DEG C. The excess of LiAlH4 was destroyed very cautiously by a saturated solution of NH4Cl. The organic layer was removed and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried (Na2CO3) and evaporated, obtaining an orange oil that was purified by column chromatography, eluting with EtOAc/MeOH (90/10). <1>H NMR (CD3OD): delta 9.20 (s, 1H), 8.02 (m, 2H), 7.53 (d, 1H, J = 8.04 Hz), 4.76 (s, 2H).

Reference： [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 270 - 273
[2]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 899 - 908
[3]Patent: EP1352910,2003,A1 .Location in patent: Page/Page column 29-30; 38

3
[ 19989-66-3 ]
[ 574-25-4 ]
6-(benzothiazol-6-ylmethylsulfanyl)-9-(β-D-ribofuranosyl)-9H-purine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With N-ethyl-N,N-diisopropylamine; (cyanomethyl)trimethyl-phosphonium iodide; In N,N-dimethyl-formamide; propiononitrile; at 90℃; for 18h;Heating / reflux;	[0165] The benzothiazole derivative was prepared as shown in Scheme 5. Ethyl benzothiazole-6-carboxylate 39 was prepared by ring closure of ethyl-4-amino-3-mercaptobenzoate.<xiv> Reduction of this ester under standard conditions at 0 DEG C gave alcohol 40.<xv> Again Mitsunobu coupling of <strong>[574-25-4]6-mercaptopurine riboside</strong> with 40 gave nucleoside 41 in 56% yield.; [0166] i) LiAlH4/THF, overnight; ii) <strong>[574-25-4]6-mercaptopurine riboside</strong>, DIPEA, propionitrile, reflux, 18 h.; [0199] (Cyanomethyl)trimethylphosphonium iodide (45 mg) was added to a mixture of 40<xiv> (33 mg, 0.2 mmol), <strong>[574-25-4]6-mercaptopurine riboside</strong> (42 mg, 0.2 mmol) and DIPEA (0.04 ml) in 0.43 ml of propionitrile. The mixture was heated at 90 DEG C and few drops of DMF were added to obtain a clear solution. Stirring was continued overnight at 90 DEG C. The mixture was cooled to rt, water was added and slowly a pale brown precipitate was formed. The solid was collected and dried in vacuo. <1>H NMR (CD3OD): delta 9.20, 8.74 (2x s, 2H), 8.59 (s, 1), 8.18 (s, 1H), 7.98 (d, 1H, J = 8.78 Hz), 7.67 (d, 1H, J = 8.77 Hz), 6.07 (d, 1H, J = 5.11 Hz), 4.84 (s, 2H), 4.72 (m, 1H), 4.35 (m, 1H), 4.17 (m, 2H), 3.83 (m, 1H); <13>C- NMR (CDCl3/d6-DMSO): delta 161.5, 157.1, 153.5, 152.8, 149.5, 144.6, 137.4, 135.2, 129.0, 124.0, 123.7, 90.6, 87.6, 75.7, 72.2, 63.0, 33.2, 19.4; Mp = decomp. 140 DEG C; HRMS calc. for C18H18N5O4S2 m/z = 432.5100 (M+H), found 432.0787.

Reference： [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 899 - 908
[2]Patent: EP1352910,2003,A1 .Location in patent: Page/Page column 29-30; 38

4
[ 19989-66-3 ]
[ 151-50-8 ]
[ 1006875-95-1 ]

Yield	Reaction Conditions	Operation in experiment
	In water; N,N-dimethyl-formamide; at 0℃; for 0.5h;ethylene glycol/water (4/1)/dry ice bath;	A solution of potassium cyanide (0.68 g, 0.010 mol) in water (3.0 mL) was added under nitrogen to a cooled (with an ethylene glycol/water (4/1)/dry ice bath) solution of <strong>[19989-66-3]1,3-benzothiazol-6-ylmethanol</strong> in DMF (30 mL). The reaction mixture was warmed to 0 C., and stirred for 30 min. Water was added and the reaction mixture was extracted with DCM. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was flash chromatographed on a silica gel column with ethyl acetate in hexane from 10-30% to afford the desired product (1.07 g). Analytical LCMS: (M+H)+=175.2.

Reference： [1]Patent: US2008/39457,2008,A1 .Location in patent: Page/Page column 43

5
[ 19989-66-3 ]
[ 19989-68-5 ]

Reference： [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 270 - 273

6
[ 114224-05-4 ]
[ 19989-66-3 ]

Reference： [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 270 - 273

7
[ 19989-66-3 ]
[ 499770-85-3 ]

Yield	Reaction Conditions	Operation in experiment
51%	With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20℃;	To an ice-cold solution of 71c (607 mg, 3.68 mmol), CBr4 (1.33 g, 4.02 mmol) and DCM (4 mL) was added dropwise a solution of triphenylphosphine (1.05 g, 4.01 mmol) in DCM (4 mL). The resulting solution was gradually warmed to RT and stirred overnight. The crude reaction mixture was concentrated and chromatographed on SiO2 eluting with a EtOAc/hexane gradient (10 to 15% EtOAc) to afford 430 mg (51%)of 71d as white solid: 1H NMR (300 MHz, CDCl3): 9.02 (s, 1H), 8.10 (d, 1H, J=8.5 Hz), 7.99 (d, 1H, J=1.8 Hz), 7.55 (1H, dd, J=8.5 Hz, 1.8 Hz), 4.65 (s, 2H).
	With hydrogen bromide; In acetic acid; at 60℃; for 2.0h;	Example 50F 6-bromomethylbenzothiazole To a 50 mL round bottom flask was added benzothiazole-6-methanol (1.0 g, 6 mmol) and 10 mL of 30 HBr in acetic acid, 50 mmol and the solution was heated to 60 C. for 2 hours. The solution was cooled to ambient and purged with nitrogen. Toluene (30 mL) was added and the solution was concentrated under vacuum (repeat 2*). The solid obtained was dried under reduced pressure at 25 C. for 16 hours to provide the title compound. 1H NMR (300 MHz, DMSO-D6) delta ppm 4.89 (s, 2H), 7.62 (dd, 1H), 8.08 (d, 1H), 8.27 (d, 1H), 9.43 (s, 1H); MS (ESI) 229 (M+H)+.

Reference： [1]Patent: US2006/40927,2006,A1 .Location in patent: Page/Page column 38
[2]Patent: US2005/209274,2005,A1 .Location in patent: Page/Page column 36

8
[ 73931-63-2 ]
[ 19989-66-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78℃; for 2.0h;	To a mixture of compound B-182 (5.0 g, 26 mmol) in anhydrous tetrahydrofuran (50 mL) was added DIBAL-H (50 mL, 1 .0 M in hexane) dropwise at -78 C. The mixture was stirred at -78 C for 2 hours. On completion, the reaction was quenched with water (50 mL) at 0 C and filtered, and the resulting filtrate was extracted with dichloromethane (3 x 100 mL). The combined organic layers were concentrated in vacuo to give compound B-183 (3.5 g, 81% yield) as a yellow oil.
61%		To a solution of 71b (194 mg, 1.01 mmol) and DCM (4 mL) cooled to -78 C. was added dropwise DIBAL-H (3.0 mL, 1.0M in DCM) and the resulting solution was gradually warmed to RT and stirred overnight. The reaction mixture was cooled to 0 C., carefully quenched with a saturated sodium potassium tartrate solution and stirred for 1 h. The solution was thrice extracted with DCM and the combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was chromatographed on SiO2 eluting with 35% EtOAc/hexane to afford 100 mg (61%) of 71c as a yellow oil (61%): 1H NMR (300 MHz, CDCl3): 8.95 (s, 1H), 8.07 (d, 1H, J=8.4 Hz), 7.96 (s, 1H), 7.47 (dd, 1H, J=8.4, 1.7 Hz), 4.84 (s, 2H).
	With diisobutylaluminium hydride; In dichloromethane; at 0 - 20℃; for 4.0h;	Example 50E benzothiazole-6-methanol To a 500 mL round bottom flask containing benzothiazole-6-carboxylic acid methyl ester (3.0 g, 15.5 mmol) and 100 mL dichloromethane at 0 C. was added diisobutylaluminum hydride (50 mL of 1.0 M solution in heptane). The solution was allowed to warm to ambient temperature and stirred for 4 hours. The mixture was diluted with ethyl acetate (100 mL), followed by stirring with sat. potassium sodium tartrate (100 mL) for 2 hours. The layers were separated, and the organic layer was washed with brine (100 mL), dried (Na2SO4), filtered and solvents were removed under reduced pressure. Purification by silica gel chromatography (25% Ethyl acetate/hexanes) provided the title compound as an oil. MS (ESI) m/z 166 [M+H]+.

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 6404 - 6410
[2]Patent: WO2015/66371,2015,A1 .Location in patent: Paragraph 00366-00367
[3]Patent: US2006/40927,2006,A1 .Location in patent: Page/Page column 38
[4]Patent: US2005/209274,2005,A1 .Location in patent: Page/Page column 36

10
[ 3622-35-3 ]
[ 19989-66-3 ]