56354-98-4|6-Aminobenzo[d]thiazol-2(3H)-one| Ambeed

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Quality Control of [ 56354-98-4 ] Purity: 97% SDS Specification

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Product Details of [ 56354-98-4 ]

CAS No. :	56354-98-4
Formula :	C₇H₆N₂OS
M.W :	166.20
SMILES Code :	NC1=CC2=C(NC(=O)S2)C=C1
MDL No. :	MFCD07792930
InChI Key :	CLYCLRFHPKKUBR-UHFFFAOYSA-N
Pubchem ID :	6453329

Safety of [ 56354-98-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 56354-98-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	2.0
Molar Refractivity	46.85
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	87.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.02
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.08
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.18
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.69
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.57
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.31

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.16
Solubility	1.16 mg/ml ; 0.00698 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.5
Solubility	0.524 mg/ml ; 0.00315 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.51
Solubility	0.514 mg/ml ; 0.00309 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.55 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.17

Application In Synthesis of [ 56354-98-4 ]

* 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 [ 56354-98-4 ]

[ 56354-98-4 ] Synthesis Path-Downstream 1~35

1
[ 56354-98-4 ]
[ 43204-63-3 ]
[ 99111-45-2 ]

References: [1]Chemical and Pharmaceutical Bulletin,1988,vol. 36,p. 2401 - 2409.

2
[ 56354-98-4 ]
[ 99111-46-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,1988,vol. 36,p. 2401 - 2409.

3
[ 56354-98-4 ]
[ 214470-55-0 ]
6,7-dimethoxy-4-(2-oxo-2,3-dihydro-benzothiazol-6-ylamino)-quinoline-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine hydrochloride; In 1-ethoxyethanol; for 0.333333h;Heating / reflux; Alkaline conditions;	A mixture of 0.249 g of 4-chloro-6,7-dimethoxy-quinolin-3-carbonitrile, 0.166 g of <strong>[56354-98-4]6-amino-2-benzothiazolinone</strong>, 0.020 g of pyridine hydrochloride, and 10 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 20 minutes. The mixture was cooled and added to 40 ml of water. To this mixture was added sodium carbonate and concentrated hydrochloric acid to adjust pH to 7. The product was collected, washed with water, and dried to give 0.326 g of 6,7-dimethoxy-4-(2-oxo-2,3-dihydro-benzothiazol-6-ylamino)-quinoline-3-carbonitrile as a solid, mp 285-287C; mass spectrum (electrospray, m/e): M+H 379.0858.

References: [1]Patent: EP1117659,2003,B1 .Location in patent: Page 74.

Yield	Reaction Conditions	Operation in experiment
		Step B 6-Amino-1,3-benzothiazol-2(3H)-one The compound obtained in Step A (0.036 mol) is dissolved in 90 ml of methanol, and then 2.5 g of palladium-on-carbon and 18 g of ammonium formate are added in succession and the mixture is heated at reflux for 18 hours. 40 ml of dioxane are added and refluxing is continued for 24 hours. The palladium-on-carbon is then filtered off. The reaction mixture is concentrated, the resulting precipitate is filtered off, and the filtrate is evaporated under reduced pressure. The resulting residue is taken up in a 1N hydrochloric acid solution and extracted twice with 50 ml of ethyl acetate each time. The aqueous phase is rendered alkaline with a 10% potassium carbonate solution and extracted twice with 50 ml of ethyl acetate each time. The organic phase is dried and then evaporated under reduced pressure, and the resulting precipitate is recrystallized from acetonitrile. Melting point: 220-224 C.

5
[ 104-53-0 ]
[ 56354-98-4 ]
6-(3-phenylpropyl)amino-2-benzothiazolone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 8 6-(3-Phenylpropyl)amino-2-benzothiazolone By reaction of <strong>[56354-98-4]6-amino-2-benzothiazolone</strong> (1.66 g) with 3-phenylpropanal using the procedure of Example 1, the title compound (0.82 g) was prepared. m.p.: 145-149 C. IR(Nujol): 3400, 1650, 1610, 1590 cm-1. NMR (CDCl3): 1.70-2.20 (m, 2H), 2.50-3.30 (m, 4H), 4.10-4.50 (m, 1H), 6.30-7.00 (m, 3H), 7.20 (s, 5H), 10.70-11.20 (m, 1H).

References: [1]Patent: US4904685,1990,A .

6
[ 56354-98-4 ]
[ 7518-70-9 ]
[ 214470-55-0 ]
6,7-dimethoxy-4-(2-oxo-2,3-dihydro-benzothiazol-6-ylamino)-quinoline-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; pyridine hydrochloride; sodium carbonate; In water;	EXAMPLE 131 6,7-Dimethoxy-4-(2-oxo-2,3-dihydro-benzothiazol-6-ylamino)-quinoline-3-carbonitrile A mixture of 0.249 g of 4-chloro-6,7-dimethoxy-quinolin-3-carbonitrile, 0.166 g of <strong>[56354-98-4]6-amino-2-benzothiazolinone</strong>, 0.020 g of pyridine hydrochloride, and 10 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 20 minutes. The mixture was cooled and added to 40 ml of water. To this mixture was added sodium carbonate and concentrated hydrochloric acid to adjust pH to 7. The product was collected, washed with water, and dried to give 0.326 g of 6,7-dimethoxy-4-(2-oxo-2,3-dihydro-benzothiazol-6-ylamino)-quinoline-3-carbonitrile as a solid, mp 285-287 C.; mass spectrum (electrospray, m/e): M+H 379.0858.

References: [1]Patent: US6288082,2001,B1 .

7
[ 1217244-19-3 ]
[ 56354-98-4 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid;	A procedure for making 6-aminobenzo[

References: [1]Patent: WO2010/30891,2010,A2 .Location in patent: Page/Page column 61.

8
[ 56354-98-4 ]
[ 496055-77-7 ]

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 2295 - 2309.

9
[ 56354-98-4 ]
C₉H₅ClN₂O₃S [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 2295 - 2309.

10
[ 56354-98-4 ]
[ 496055-75-5 ]

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 2295 - 2309.

11
[ 56354-98-4 ]
[ 4755-77-5 ]
[ 496055-74-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium acetate; acetic acid; at 35 - 90℃; for 1.75h;	General procedure: 6-Amino-3H-1,3-benzoxazol-2-one (700 mg, 4.66 mmol) and sodium acetate (497 mg, 6.05 mmol) were dissolved in acetic acid (20 mL) at 35 C. Ethyl chlorooxoacetate (677 muL, 6.05 mmol) was added dropwise and the reaction mixture was stirred at 35 C for 1 h and 45 min at 90 C then water (50 mL) was added to the solution. The precipitate was filtered, washed with water (2 × 30 mL) and dried overnight under vacuum in presence of P2O5 to afford the intermediate ethyl 2-acetamido-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetate (857 mg, 74%) as a white solid. A solution of potassium hydroxide (101 mg, 1.80 mmol) in water (400 muL) was added to a suspension of ethyl 2-acetamido-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetate obtained above (150 mg, 0.60 mmol) in ethanol (3 mL) and the reaction mixture was stirred at room temperature for 2 h. Water (5 mL) was added to the mixture and the resulting homogenous solution was acidified to pH = 1 with concentrated HCl. The precipitate was filtered and dried overnight under vacuum in presence of P2O5 to give 4a (115 mg, 87%) as a white solid.

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 2295 - 2309.

12
(RS)-ethyl 4-chloro-5, 6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxylate [ No CAS ]
[ 56354-98-4 ]
(RS)-ethyl 4-[(2-oxo-2,3-dihydro-1,3-benzothiazol-6-yl)amino]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxylate HCl salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With hydrogenchloride; In 1,4-dioxane; ethanol; at 100℃; for 5h;	General procedure: A mixture comprising 1.00 g (3.37 mmol) (RS)-ethyl 4-chloro-5, 6,7,8- tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxylate which was prepared according to intermediate example 1a, 840 mg 6-amino-1 ,3-benzothiazol-2(3H)- one, 9.54 mL ethanol and 182 muIota_ hydrochloric acid (4M in dioxane) was reacted at 100C for 5 hours. The precipitate was washed with ethanol and diethyl ether and digested with hydrochloric acid (1M). After filtration the solid was washed with water, propan-2-ol, diethyl ether and dried to give 1.24 g (76%) of the title compound as hydrochloride.1H-NMR (DMSO-d6): delta= 1.18 (3H), 1.90 (1 H), 2.17 (1 H), 2.86-3.22 (5H), 4.09 (2H), 7.10 (1 H), 7.40 (1 H), 7.77 (1 H), 8.36 (1 H), 8.45 (1 H), 11.91 (1 H) ppm.

References: [1]Patent: WO2013/174735,2013,A1 .Location in patent: Page/Page column 65.

13
[ 56354-98-4 ]
[ 5399-92-8 ]
[ 1584150-66-2 ]

Yield	Reaction Conditions	Operation in experiment
24%	With hydrogenchloride; In 1,4-dioxane; ethanol; at 110℃; for 10h;	General procedure: A mixture comprising 60.0 mg (307 mumol) 4-chloro-6-ethyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (prepared according to intermediate exampLe 1a), 51 mg <strong>[56354-98-4]6-amino-1,3-benzothiazol-2(3H)-one</strong> (CAS-No: 56354-98-4), 1.75 mL ethanol and 16.9 muL hydrochloric acid (4M in dioxane) was reacted at 110C for 10 hours. The residue was digested in a mixture of diethyl ether and ethanol and dried to give 85.3 mg (85%) of the title compound.

References: [1]Patent: WO2014/44691,2014,A1 .Location in patent: Page/Page column 68; 71.

14
[ 56354-98-4 ]
[ 784150-41-0 ]
[ 1584150-67-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogenchloride; In 1,4-dioxane; ethanol; at 110℃; for 10h;	General procedure: A mixture comprising 60.0 mg (307 mumol) 4-chloro-6-ethyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (prepared according to intermediate exampLe 1a), 51 mg <strong>[56354-98-4]6-amino-1,3-benzothiazol-2(3H)-one</strong> (CAS-No: 56354-98-4), 1.75 mL ethanol and 16.9 muL hydrochloric acid (4M in dioxane) was reacted at 110C for 10 hours. The residue was digested in a mixture of diethyl ether and ethanol and dried to give 85.3 mg (85%) of the title compound.

References: [1]Patent: WO2014/44691,2014,A1 .Location in patent: Page/Page column 68; 72.

15
[ 56354-98-4 ]
[ 784150-41-0 ]
[ 1584150-82-2 ]

References: [1]Patent: WO2014/44691,2014,A1 .

16
[ 56354-98-4 ]
[ 87-42-3 ]
[ 1584150-68-4 ]

Yield	Reaction Conditions	Operation in experiment
28%	With hydrogenchloride; In 1,4-dioxane; ethanol; at 110℃; for 10h;	General procedure: A mixture comprising 60.0 mg (307 mumol) 4-chloro-6-ethyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (prepared according to intermediate exampLe 1a), 51 mg <strong>[56354-98-4]6-amino-1,3-benzothiazol-2(3H)-one</strong> (CAS-No: 56354-98-4), 1.75 mL ethanol and 16.9 muL hydrochloric acid (4M in dioxane) was reacted at 110C for 10 hours. The residue was digested in a mixture of diethyl ether and ethanol and dried to give 85.3 mg (85%) of the title compound.

References: [1]Patent: WO2014/44691,2014,A1 .Location in patent: Page/Page column 68; 72.

17
ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate [ No CAS ]
[ 56354-98-4 ]
[ 1584150-69-5 ]

Yield	Reaction Conditions	Operation in experiment
68%	With hydrogenchloride; In 1,4-dioxane; ethanol; at 110℃; for 10h;	General procedure: A mixture comprising 60.0 mg (307 mumol) 4-chloro-6-ethyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (prepared according to intermediate exampLe 1a), 51 mg <strong>[56354-98-4]6-amino-1,3-benzothiazol-2(3H)-one</strong> (CAS-No: 56354-98-4), 1.75 mL ethanol and 16.9 muL hydrochloric acid (4M in dioxane) was reacted at 110C for 10 hours. The residue was digested in a mixture of diethyl ether and ethanol and dried to give 85.3 mg (85%) of the title compound.

References: [1]Patent: WO2014/44691,2014,A1 .Location in patent: Page/Page column 68; 72.

18
[ 56354-98-4 ]
[ 35808-68-5 ]
[ 1584150-73-1 ]

Yield	Reaction Conditions	Operation in experiment
4%	With hydrogenchloride; In 1,4-dioxane; ethanol; at 110℃; for 10h;	General procedure: A mixture comprising 60.0 mg (307 mumol) 4-chloro-6-ethyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (prepared according to intermediate exampLe 1a), 51 mg <strong>[56354-98-4]6-amino-1,3-benzothiazol-2(3H)-one</strong> (CAS-No: 56354-98-4), 1.75 mL ethanol and 16.9 muL hydrochloric acid (4M in dioxane) was reacted at 110C for 10 hours. The residue was digested in a mixture of diethyl ether and ethanol and dried to give 85.3 mg (85%) of the title compound.

References: [1]Patent: WO2014/44691,2014,A1 .Location in patent: Page/Page column 68; 74.

19
[ 56354-98-4 ]
[ 1618-36-6 ]
[ 1584150-74-2 ]

Yield	Reaction Conditions	Operation in experiment
9%	With hydrogenchloride; In 1,4-dioxane; ethanol; at 110℃; for 10h;	General procedure: A mixture comprising 60.0 mg (307 mumol) 4-chloro-6-ethyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (prepared according to intermediate exampLe 1a), 51 mg <strong>[56354-98-4]6-amino-1,3-benzothiazol-2(3H)-one</strong> (CAS-No: 56354-98-4), 1.75 mL ethanol and 16.9 muL hydrochloric acid (4M in dioxane) was reacted at 110C for 10 hours. The residue was digested in a mixture of diethyl ether and ethanol and dried to give 85.3 mg (85%) of the title compound.

References: [1]Patent: WO2014/44691,2014,A1 .Location in patent: Page/Page column 68; 75.

20
[ 56354-98-4 ]
[ 1584150-96-8 ]
[ 1584150-60-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogenchloride; In 1,4-dioxane; ethanol; at 110℃; for 10h;	A mixture comprising 60.0 mg (307 mumol) 4-chloro-6-ethyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (prepared according to intermediate exampLe 1a), 51 mg <strong>[56354-98-4]6-amino-1,3-benzothiazol-2(3H)-one</strong> (CAS-No: 56354-98-4), 1.75 mL ethanol and 16.9 muL hydrochloric acid (4M in dioxane) was reacted at 110C for 10 hours. The residue was digested in a mixture of diethyl ether and ethanol and dried to give 85.3 mg (85%) of the title compound. 1HNMR (DMSO-d6): delta = 1.16 (3H), 2.37 (3H), 2.66 (2H), 7.23 (1H), 7.37 (1H), 7.74 (1H), 8.10 (1H), 9.65 (1H), 12.18 (1H), 12.50 (1H) ppm.

References: [1]Patent: WO2014/44691,2014,A1 .Location in patent: Page/Page column 68.

21
[ 56354-98-4 ]
7-chloro-2-(cyclopropylmethyl)[1,3]thiazolo[5,4-d]pyrimidine [ No CAS ]
6-([2-(cyclopropylmethyl)[1,3]thiazolo[5,4-d]pyrimidin-7-yl]amino)-1,3-benzothiazol-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With hydrogenchloride; In 1,4-dioxane; ethanol; at 110℃;	A mixture comprising 22 mg (97 pmol) 7-chloro-2-(cyclopropylmethyl)[1 , 3]thiazolo[5,4-d]pyrimidine (prepared according tointermediate example la), 16.2 mg <strong>[56354-98-4]6-amino-1,3-benzothiazol-2(3H)-one</strong>, 0.5 mLethanol and 5.5 pL hydrochloric acid (4M in dioxane) was reacted at 110C overnight. The crude product was purified by chromatography to give 16.1 mg (44%) of the title compound. 1H-NMR (DMSO-d6): oe= 0.39 (2H), 0.64 (2H), 1.20 (1H), 3.06 (2H), 7.09 (1H), 7.69(1H), 8.09 (1H), 8.46 (1H), 10.04 (1H), 11.82 (1H) ppm.

References: [1]Patent: WO2014/135480,2014,A1 .Location in patent: Page/Page column 82.

22
[ 56354-98-4 ]
[ 946198-89-6 ]
tert-butyl 4-[(2-oxo-2,3-dihydro-1,3-benzothiazol-6-yl)amino]-5,8-dihydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7(6H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 100℃; for 16h;	Example 3 tert-Butyl 4-[(2-oxo-2,3-dihydro-1 ,3-benzothiazol-6-yl)amino]-5,8- dihydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7(6H)-carboxylate A mixture comprising 100 mg (307 muetaetaomicronIota) tert-butyl 4-chloro-5,8- dihydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7(6H)-carboxylate (prepared according to WO2009/33581 ), 51 mg 6-amino-1 ,3-benzothiazol-2(3H)-one(CAS-No: 56354-98-4), 2 ml_ dimethyl sulfoxide and 160 muIota_ N-ethyl-N-isopropylpropan-2-amine was heated at 100C for 16 hours. The crude product was purified by chromatography and crystallisation to give 40.5 mg (36%) of the title compound. 1 H-NMR (DMSO-d6): delta = 1.45 (9H), 3.20 (2H), 3.69 (2H), 4.68 (2H), 7.1 1 (1 H), 7.47 (1 H), 7.84 (1 H), 8.25 (1 H), 8.38 (1 H), 1 1.87 (1 H) ppm.

References: [1]Patent: WO2015/181063,2015,A1 .Location in patent: Page/Page column 55; 56.

23
[ 56354-98-4 ]
[ 117519-08-1 ]
6-((3-amino-6-(trifluoromethyl)pyridin-2-yl)amino)benzo[d]thiazol-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%		A solution of 2-chioro-3-nitro-6-(trifiuoromethyl)pyridine (2.0 g, 8.8 mmoi) and 6-aninobenzo[d]thiazoi-2(3H?)-one (1.5 g, 8.8 mmol) in DMF (40 ml.) was heated at 110 0Q After 3h. sodium dithionite (6.1 g, 35.3 mmoi) was added to the mixture was let stir at 110 cc for 5 h. Thereaction was diluted with water (320 mL) and let stir for 20 mm where precipitate formed. Thereaction was filtered and the solid was washed with H20 and oven dried at 45 C to give the desiredcompound as a solid (2.6 g, 90%). MS (ESI): mass caicd. for C,3HF3N4OS, 326.05 rn/z found, 327.0 [M++{]t.

References: [1]Patent: WO2016/176460,2016,A1 .Location in patent: Page/Page column 189; 190.

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[ 56354-98-4 ]
[ 353277-27-7 ]
5-nitro-6-(2-oxo-2,3-dihydrobenzo[d]thiazol-6-yl)picolinic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In ethanol; at 80℃; for 32h;	nitropicolinic acid (1.0 g, 2.5 mmoi, 50% pure), 6-amino-2(3H?)-benzothiazolone (0.92 g, 5.6 mmoi), and DIEA (1.3 mL, 7.4 mmoi) in EtOH (10 mL) was refiuxed at 80 C for 16 liTo thereaction mixture was added another portion of 6-amino2(3H)-benzothiazolone (102 mg, 0.61 mmol) and heated at 80 C for 16 h. The resulting mixture was cooled in freezer. The precipitate was filtered, washed with cold FtOH and dried under high vacuum to give a dark brovrn solid (1.5 g, 91%, 50% pure). MS (ESI): mass calcd. for C13H8N405S, 332.0; m/z found, 332.9 M+H].A solution of 6-chioro-5-

References: [1]Patent: WO2016/176460,2016,A1 .Location in patent: Page/Page column 158.

25
[ 56354-98-4 ]
[ 58602-02-1 ]
[ 100-52-7 ]
6-(5-fluoro-2-phenyl-imidazo[4,5-b]pyridin-3-yl)-3H-1,3-benzothiazol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Asolution of 2,6-difluoro-3nitropyridine (0.20g. 1.3 mrnol) and &aminobenzo[d]thiazol.-2(3H)-one (0.20 g, 1.2 mmol) in DMF (6 mL) was heated at 100 C for 1 h. Benzaldehyde (0.15 g, 1.4 mmol) was added to the mixture and the reaction was let stir for 30 mm followed by addition of sodium dithionite (0.65g. 3.8 mmoi). After 12 hat 100 C the reaction was cooled, diluted with EtOAc (50mL), and washed with H20 (25 mL x 3). The organic layer was dried (Na2504) and concentrated in vaeuo. Purification FCC. Si02, EtOAc/hexanes) afforded the title compound (0.10 g, 22%). MS (ESfl: mass caicd. for C,9H, ,FN4OS, 362.1; miz found, 363.1 [M+Hf. ?H NMR (400 MHz, DMSO-d6) oe 12.19 (br s, 11-I), 8.39 (dd, ,j:::: 8.5, 7.2 Hz. ifI). 7.79 (d, J::: 2.1 Hz, IH), 7.60 7.53 (m, 21-I), 7.48 -- 7.37 (m. 31:1), 7.31 (dd, J: 8.4. 2.1 Fiz, 11-I), 7.24 (d, ,j:::: 8.4 Hz, IH), 7,14 (dd, J::::8.5.0.8Hz, 11-I).

References: [1]Patent: WO2016/176460,2016,A1 .Location in patent: Page/Page column 154.

26
[ 56354-98-4 ]
[ 100-52-7 ]
6-[2-phenyl-5-(1-piperidyl)imidazo[4,5-b]pyridin-3-yl]-3H-1,3-benzothiazol-2-one [ No CAS ]

References: [1]Patent: WO2016/176460,2016,A1 .

27
[ 56354-98-4 ]
6-[2,5-bis(trifluoromethyl)imidazo[4,5-b]pyridin-3-yl]-3H-1,3-benzothiazol-2-one [ No CAS ]

References: [1]Patent: WO2016/176460,2016,A1 .

28
[ 56354-98-4 ]
6-(5-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-3-yl)benzo[d]thiazol-2(3H)-one [ No CAS ]

References: [1]Patent: WO2016/176460,2016,A1 .

29
[ 56354-98-4 ]
1-(2-oxo-2,3-dihydrobenzo[d]thiazol-6-yl)pyrrolidine-2,5-dione [ No CAS ]