[ CAS No. 1201633-72-8 ] {[proInfo.proName]}

Name: 1201633-72-8|2-Bromo-5,6-dihydrobenzo[d]thiazol-7(4H)-one|98%
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Product Details of [ 1201633-72-8 ]

CAS No. :	1201633-72-8	MDL No. :	MFCD13250122
Formula :	C₇H₆BrNOS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AINBODIOGRXMKN-UHFFFAOYSA-N
M.W :	232.10	Pubchem ID :	44229256
Synonyms :

Safety of [ 1201633-72-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1201633-72-8 ]

* 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 [ 1201633-72-8 ]

[ 1201633-72-8 ] Synthesis Path-Downstream 1~50

1
[ 540-80-7 ]
2-amino-5,6-dihydrobenzothiazol-7(4H)-one dihydrobromide [ No CAS ]
[ 1201633-72-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert.-butylnitrite With copper(ll) bromide In acetonitrile at 0 - 20℃; Stage #2: 2-amino-5,6-dihydrobenzothiazol-7(4H)-one dihydrobromide In acetonitrile at 20℃;

Reference： [1]Walter; Von Coburg; Isensee; Sander; Ligneau; Camelin; Schwartz; Stark [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 19, p. 5879 - 5882]

2
[ 3179-63-3 ]
[ 1201633-72-8 ]
[ 1254274-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-Dimethylamino-1-propanol With sodium hydride In tetrahydrofuran; mineral oil at 40℃; for 3h; Inert atmosphere; Stage #2: 2-bromo-5 ,6-dihydrobenzo[d]thiazol-7(4H)-one In tetrahydrofuran; mineral oil at 60℃; for 4h; Inert atmosphere;

Reference： [1]Walter; Von Coburg; Isensee; Sander; Ligneau; Camelin; Schwartz; Stark [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 19, p. 5879 - 5882]

3
[ 1201633-72-8 ]
[ 5720-05-8 ]
[ 1251924-63-6 ]

Yield	Reaction Conditions	Operation in experiment
68%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; ethanol at 140℃; Microwave irradiation;

Reference： [1]Location in patent: scheme or table Walsh, Shawn P.; Severino, Alexandra; Zhou, Changyou; He, Jiafang; Liang, Gui-Bai; Tan, Carina P.; Cao, Jin; Eiermann, George J.; Xu, Ling; Salituro, Gino; Howard, Andrew D.; Mills, Sander G.; Yang, Lihu [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 11, p. 3390 - 3394]

4
[ 17583-10-7 ]
[ 1201633-72-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With copper(ll) bromide; isopentyl nitrite; In acetonitrile; at 80℃; for 1h;	A mixture of <strong>[17583-10-7]2-amino-5,6-dihydro-4H-benzothiazol-7-one</strong> (19 g, 112 mmol), copper (II) bromide (27 g, 120 mmol) and 3-methyl-l-nitrosooxy-butane (18 g, 153 mmol) in ACN (250 mL) was heated at 80°C for 1 hour. The reaction mixture was then cooled to room temperature and poured into a 10percent solution of HC1. The mixture was extracted with DCM and the organic layer was separated, dried (Na2S04), filtered and the solvent evaporated in vacuo to yield 19.6 g (75percent) of intermediate 1 that was used in the next step without further purification.
	With copper(ll) bromide; isopentyl nitrite; In acetonitrile; at 80℃; for 1h;	A mixture of <strong>[17583-10-7]2-amino-5,6-dihydro-4H-benzothiazol-7-one</strong> (19 g, 112 mmol), copper (II) bromide (27 g, 120 mmol) and 3-methyl-1-nitrosooxy-butane (18 g, 153 mmol) in ACN (250 mL) was heated at 80° C. for 1 hour. The reaction mixture was then cooled to room temperature and poured into a 10percent solution of HCl. The mixture was extracted with DCM and the organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo to yield 19.6 g (75percent) of intermediate 1 that was used in the next step without further purification.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3390 - 3394
[2]Patent: WO2011/73347,2011,A1 .Location in patent: Page/Page column 32
[3]Journal of Medicinal Chemistry,2013,vol. 56,p. 7243 - 7259
[4]Patent: US2012/252800,2012,A1 .Location in patent: Page/Page column 14

5
[ 1201633-72-8 ]
[ 536-74-3 ]
[ 1312412-56-8 ]

Yield	Reaction Conditions	Operation in experiment
52%	With copper(l) iodide; triethylamine In 1,4-dioxane for 2h; Inert atmosphere; Reflux;	B1 To a solution of intermediate 1 (2.3 g, 9.86 mmol), phenylacetylene (2.01 g, 19.7 mmol), copper (I) iodide (0.2 g, 1.05 mmol) and triethylamine (2.98 g, 29.58 mmol) in 1 ,4-dioxane (50 mL) at room temperature was added [ 1 , Γ- bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (0.2 g, 0.245 mmol). The reaction mixture was stirred at reflux for 2 hours under a nitrogen atmosphere. The reaction mixture was then cooled to room temperature and the volatiles were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; petroleum ether/ AcOEt 1 :2). The desired fractions were collected and the solvent was evaporated in vacuo to yield 1.2 g (52%) of compound 1 as a solid.1H NMR (400 MHz, CDC13) δ ppm 2.28 (quin, J=6.4 Hz, 2 H), 2.70 (t, J=6.3 Hz, 2 H), 3.13 (t, J=6.1 Hz, 2 H), 7.39 - 7.53 (m, 3 H), 7.60 - 7.70 (m, 2 H).
52%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; triethylamine In 1,4-dioxane at 20℃; for 2h; Reflux; Inert atmosphere;
	With copper(l) iodide; triethylamine In 1,4-dioxane for 2h; Reflux; Inert atmosphere;	B.1 To a solution of intermediate 1 (2.3 g, 9.86 mmol), phenylacetylene (2.01 g, 19.7 mmol), copper (I) iodide (0.2 g, 1.05 mmol) and triethylamine (2.98 g, 29.58 mmol) in 1,4-dioxane (50 mL) at room temperature was added [1,1'-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (0.2 g, 0.245 mmol). The reaction mixture was stirred at reflux for 2 hours under a nitrogen atmosphere. The reaction mixture was then cooled to room temperature and the volatiles were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; petroleum ether/AcOEt 1:2). The desired fractions were collected and the solvent was evaporated in vacuo to yield 1.2 g (52%) of compound 1 as a solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.28 (quin, J=6.4 Hz, 2H), 2.70 (t, J=6.3 Hz, 2H), 3.13 (t, J=6.1 Hz, 2H), 7.39-7.53 (m, 3H), 7.60-7.70 (m, 2H).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2011/73347, 2011, A1 Location in patent: Page/Page column 38
[2]Bartolomé-Nebreda, José Manuel; Conde-Ceide, Susana; Delgado, Francisca; Iturrino, Laura; Pastor, Joaquín; Pena, Miguel Ángel; Trabanco, Andrés A.; Tresadern, Gary; Wassvik, Carola M.; Stauffer, Shaun R.; Jadhav, Satyawan; Gogi, Kiran; Vinson, Paige N.; Noetzel, Meredith J.; Days, Emily; Weaver, C. David; Lindsley, Craig W.; Niswender, Colleen M.; Jones, Carrie K.; Conn, P. Jeffrey; Rombouts, Frederik; Lavreysen, Hilde; Macdonald, Gregor J.; Mackie, Claire; Steckler, Thomas [Journal of Medicinal Chemistry, 2013, vol. 56, # 18, p. 7243 - 7259]
[3]Current Patent Assignee: JOHNSON & JOHNSON INC - US2012/252800, 2012, A1 Location in patent: Page/Page column 17

6
[ 1201633-72-8 ]
[ 6783-05-7 ]
[ 1312412-60-4 ]

Yield	Reaction Conditions	Operation in experiment
52%	With sodium carbonate In 1,2-dimethoxyethane; water at 80℃; Inert atmosphere;	B5 To a solution of intermediate 1 (0.6 g, 2.6 mmol), tra/?s-2-phenylboronic acid (0.38 g, 2.6 mmol) and Na2C03 (0.54 g, 5.2 mmol) in 1 ,2-dimethoxyethane (9 mL) and H20 (3 mL), at room temperature, was added Pd(PPh3)4 (0.09 g, 0.06 mmol). The reaction mixture was stirred at 80°C overnight under a nitrogen atmosphere. The reaction mixture was then cooled to room temperature, diluted with H20 (15 mL) and extracted with AcOEt (15 mL). The organic layer was separated, dried (Na2S04), filtered and the solvent evaporated in vacuo. The crude product was purified by columnchromatography (silica; petroleum ether/ AcOEt 5 : 1). The desired fractions were collected and the solvent was evaporated in vacuo to yield compound 5 (350 mg, 52% yield).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2011/73347, 2011, A1 Location in patent: Page/Page column 40

7
[ 519054-54-7 ]
[ 1201633-72-8 ]
[ 1312412-64-8 ]

Yield	Reaction Conditions	Operation in experiment
11%	With sodium carbonate In 1,2-dimethoxyethane; water at 80℃; Inert atmosphere;	B9 Pd(PPh3)4 (0.03 g, 0.02 mmol) was added to a solution of intermediate 1 (0.2 g, 0.865 mmol), 4-methyl-7-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H- benzo[l,4]oxazine (0.23 g, 0.865 mmol) and Na2C03 (0.23 g, 0.865 mmol) in a mixture of 1 ,2-dimethoxyethane (3 mL) and H20 (lmL) at room temperature. The reaction mixture was stirred at 80°C overnight under a nitrogen atmosphere, then cooled to room temperature and AcOEt (5 mL) added. The organic layer was separated, washed with H20, dried (Na2S04) and the solvent evaporated in vacuo. The residue thus obtained was purified by reverse phase HPLC (gradient elution: 0.1% TFA in ACN/0.1% TFA in H20). The desired fractions were collected, washed with NaHC03 (aqueous saturated solution) and extracted with AcOEt (2 x 100 mL). The combined organic extracts were dried (Na2S04) and evaporated in vacuo affording compound 9 (28 mg, 11% yield).1H NMR (300 MHz, CDCL3) δ ppm 2.09 - 2.22 (m, 2 H), 2.51 - 2.59 (m, H), 2.92 (s, 3 H), 3.00 (t, J=6.1 Hz, 2 H), 3.30 - 3.36 (m, 2 H), 4.20 - 4.25 (m, 2 H), 6.58 (d, J=8.3 Hz, 1 H), 7.34 (d, J=2.3 Hz, 1 H), 7.47 - 7.54 (m, 1 H).
	With sodium carbonate In 1,2-dimethoxyethane; water at 20 - 80℃; Inert atmosphere;	B.9 Pd(PPh3)4 (0.03 g, 0.02 mmol) was added to a solution of intermediate 1 (0.2 g, 0.865 mmol), 4-methyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[1,4]oxazine (0.23 g, 0.865 mmol) and Na2CO3 (0.23 g, 0.865 mmol) in a mixture of 1,2-dimethoxyethane (3 mL) and H2O (1 mL) at room temperature. The reaction mixture was stirred at 80° C. overnight under a nitrogen atmosphere, then cooled to room temperature and AcOEt (5 mL) added. The organic layer was separated, washed with H2O, dried (Na2SO4) and the solvent evaporated in vacuo. The residue thus obtained was purified by reverse phase HPLC (gradient elution: 0.1% TFA in ACN/0.1% TFA in H2O). The desired fractions were collected, washed with NaHCO3 (aqueous saturated solution) and extracted with AcOEt (2×100 mL). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo affording compound 9 (28 mg, 11% yield). 1H NMR (300 MHz, CDCL3) δ ppm 2.09-2.22 (m, 2H), 2.51-2.59 (m, 2 H), 2.92 (s, 3H), 3.00 (t, J=6.1 Hz, 2H), 3.30-3.36 (m, 2H), 4.20-4.25 (m, 2H), 6.58 (d, J=8.3 Hz, 1H), 7.34 (d, J=2.3 Hz, 1H), 7.47-7.54 (m, 1H).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2011/73347, 2011, A1 Location in patent: Page/Page column 42-43
[2]Current Patent Assignee: JOHNSON & JOHNSON INC - US2012/252800, 2012, A1 Location in patent: Page/Page column 19

8
[ 1201633-72-8 ]
[ 1312412-91-1 ]
[ 1312412-57-9 ]

Yield	Reaction Conditions	Operation in experiment
43%	In tetrahydrofuran at 20℃; for 14h; Inert atmosphere;	B2 To a solution of intermediate 1 (0.2 g, 0.86 mmol), intermediate 8 (0.25 g, 1.29 mmol), copper (I) iodide (0.006 g, 0.034 mmol) and PdCl2(PPh3)2 (0.012 g, 0.017 mmol) in THF (8 mL) at room temperature was added tetrabutylammonium fluoride (2.58 mL, 2.58 mmol; 1M solution in THF) under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 14 hours then concentrated in vacuo. The crude product was purified by flash column chromatography (silica; petroleum ether/ AcOEt 5: 1). The desired fractions were collected and the solvent was evaporated in vacuo to yield compound 2 (101.5 mg, 43% yield) as a yellow solid.1H NMR (300 MHz, CDC13) δ ppm 2.19 (quin, J=6.4 Hz, 2 H), 2.50 - 2.72 (m, 2 H), 3.04 (t, J=6.2 Hz, 2 H), 7.55 (dd, J=8.3, 1.3 Hz, 1 H), 8.50 (br. s., 1 H), 8.63 (br. s., 1 H).
	With copper(l) iodide; tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 14h; Inert atmosphere;	B.2 To a solution of intermediate 1 (0.2 g, 0.86 mmol), intermediate 8 (0.25 g, 1.29 mmol), copper (I) iodide (0.006 g, 0.034 mmol) and PdCl2(PPh3)2 (0.012 g, 0.017 mmol) in THF (8 mL) at room temperature was added tetrabutylammonium fluoride (2.58 mL, 2.58 mmol; 1M solution in THF) under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 14 hours then concentrated in vacuo. The crude product was purified by flash column chromatography (silica; petroleum ether/AcOEt 5:1). The desired fractions were collected and the solvent was evaporated in vacuo to yield compound 2 (101.5 mg, 43% yield) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ ppm 2.19 (quin, J=6.4 Hz, 2H), 2.50-2.72 (m, 2H), 3.04 (t, J=6.2 Hz, 2H), 7.55 (dd, J=8.3, 1.3 Hz, 1H), 8.50 (br. s., 1H), 8.63 (br. s., 1H).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2011/73347, 2011, A1 Location in patent: Page/Page column 39
[2]Current Patent Assignee: JOHNSON & JOHNSON INC - US2012/252800, 2012, A1 Location in patent: Page/Page column 17

9
[ 1201633-72-8 ]
C₈H₉BO₂ [ No CAS ]
[ 1312412-60-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In 1,2-dimethoxyethane; water at 20 - 80℃; Inert atmosphere;	B.5 To a solution of intermediate 1 (0.6 g, 2.6 mmol), trans-2-phenylboronic acid (0.38 g, 2.6 mmol) and Na2CO3 (0.54 g, 5.2 mmol) in 1,2-dimethoxyethane (9 mL) and H2O (3 mL), at room temperature, was added Pd(PPh3)4 (0.09 g, 0.06 mmol). The reaction mixture was stirred at 80° C. overnight under a nitrogen atmosphere. The reaction mixture was then cooled to room temperature, diluted with H2O (15 mL) and extracted with AcOEt (15 mL). The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica; petroleum ether/AcOEt 5:1). The desired fractions were collected and the solvent was evaporated in vacuo to yield compound 5 (350 mg, 52% yield).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2012/252800, 2012, A1 Location in patent: Page/Page column 18

10
[ 1201633-72-8 ]
C₈H₉BO₂ [ No CAS ]
[ 1312412-61-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,2-dimethoxyethane; water / 20 - 80 °C / Inert atmosphere 2: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 20 °C

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2012/252800, 2012, A1

11
[ 1201633-72-8 ]
2-bromo-7-methylene-4,5,6,7-tetrahydrobenzo[d]thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60.5%	With n-butyllithium In tetrahydrofuran at -78℃;	25.a Synthesis of 2-bromo-7-methylene-4,5,6,7-tetrahydrobenzo[d]thiazole To a stirred solution of Ι,Γ-biphenyl compound with bromo(methylene)(phenyl)phosphorane (1 : 1) (400 mg, 1.120 mM) dissolved in dry THF (10 ml), -butyllithium was added (646 μ, 1.034 mM) at -78 C and allowed to stir for 30-40 min. 2-bromo-5,6-dihydrobenzo[d]thiazol-7(4H)-one (200 mg, 0.862 mM) was slowly added to the mixture and the mixture was allowed to stir at room temperature for 3-5 h. After completion of reaction, the mixture was quenched with ammonium chloride, extracted with ethyl acetate, concentrated and purified by column chromatography to give the title compound. Yield: 120 mg, 0.521 mM, 60.5 ; JH NMR (300 MHz, CDC13) δ: 5.00 (s, 1H), 4.93 (s, 1H), 2.84 (t, / = 6.3 Hz, 2H), 2.51-2.47 (m, 2H), 1.96-1.88 (m, 2H); HPLC: 73.96%; MS (E/Z): 229.9 (M+).

Reference： [1]Current Patent Assignee: PIRAMAL ENTERPRISES LIMITED - WO2015/125085, 2015, A1 Location in patent: Page/Page column 74

12
C₇H₈N₂OS*(x)ClH [ No CAS ]
[ 1201633-72-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With tert.-butylnitrite; copper(ll) bromide In acetonitrile for 1.5h;	Intermediate 1 43B: 2-bromo-5 ,6-dihydrobenzo[djthiazol-7(4H)-one Copper(II) bromide (1.466 g, 6.56 mmol) and t-butyl nitrite (0.780 mL, 6.56mmol) were dissolved in MeCN (15.44 mL) and allowed to stir 10 minutes. Intermediate143A (0.79 g, 3.86 mmol) was dissolved in MeCN (23.16 mL) and the copper solutionwas added and the reaction mixture was stirred for 1.5 hours. The reaction mixture wasconcentrated in vacuo. The residue was dissolved in EtOAc, washed twice with 1 N HC1,saturated NaHCO3, then brine, dried (Na2504), filtered, and concentrated in vacuo to giveIntermediate 143B (817.9 mg, 3.52 mmol, 91%) as an orange solid: ‘H NMR (400MHz,CHLOROFORM-d) 3.07 (t, J6.2 Hz, 2H), 2.64 (dd, J7.3, 5.7 Hz, 2H), 2.24 (quin,J=6.4 Hz, 2H); LC-MS: Method H, RT = 0.98 mm, MS (ESI) m/z: 232/234 (M+H)t

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2018/13774, 2018, A1 Location in patent: Page/Page column 543

13
[ 1201633-72-8 ]
2-bromo-4,5,6,7-tetrahydrobenzo[d]thiazol-7-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With methanol; sodium tetrahydroborate at 0℃; for 1.5h;	143 Intermediate 143 C: 2-bromo-4,5,6,7-tetrahydrobenzo [djthiazol-7-ol Intermediate 143B (500 mg, 2.154 mmol) was dissolved in MeOH (10.8 mL) and cooled to 0 °C. Sodium borohydride (163 mg, 4.31 mmol) was added and stirred for 1.5 hours. The reaction mixture was quenched with saturated ammonium chloride andextracted with EtOAc. The organic layer was washed with water, then brine, dried (Na2SO4), filtered, and concentrated in vacuo to give Intermediate 143C (488 mg, 2.084 mmol, 97%) as an orange oil: ‘H NMR (400MHz, CHLOROFORM-d) 4.93 (br. s., 1H), 2.89-2.79 (m, 1H), 2.79-2.69 (m, 1H), 2.17-2.07 (m, 1H), 2.06-1.98 (m, 1H), 1.92-1.80 (m, 2H); LC-MS: Method H, RT = 0.88 mm, MS (ESI) m/z: 234/236 (M+H)

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2018/13774, 2018, A1 Location in patent: Page/Page column 543; 544

14
[ 60060-44-8 ]
[ 1201633-72-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine / ethanol / 20 °C / Reflux 2: tert.-butylnitrite / acetonitrile / 12 h / Reflux
	Multi-step reaction with 2 steps 1: pyridine / ethanol / Reflux 2: copper (II) bromide; tert.-butylnitrite / acetonitrile / Reflux

Reference： [1]Current Patent Assignee: NANKAI UNIVERSITY - CN111689927, 2020, A
[2]Bian, Qiang; Peng, Xing-Jie; Tian, Xue-Rong; Zhao, Tong-Tong; Zhao, Wei-Guang [Journal of Heterocyclic Chemistry, 2022]

15
[ 1201633-72-8 ]
[ 57260-71-6 ]
4-(7-oxo-4,5,6,7-tetrahydrobenzothiazol-2-yl)piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73.3%	In isopropyl alcohol at 85℃; for 10h;	3 Synthesis of 4-(7-oxo-4,5,6,7-tetrahydrobenzothiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester 5 Take 2-bromo-5,6-dihydro-4H-benzothiazol-7-one 3 (18.5g, 79.7mmol) and add it to 400mL of isopropanol solvent. While stirring at room temperature, add 1-(tert Butoxycarbonyl)piperazine 4 (29.7g, 159.4mmol), heated to 85°C, heated to reflux for 10h, TLC monitored until the reaction was completed, the reaction solution was cooled down, and the solvent was removed to obtain an oily substance. Add 1L ethyl acetate and 500ml water, and divide The organic layer was washed with 500mL*2 saturated sodium bicarbonate and 500mL of water. The organic layer was dried with anhydrous magnesium sulfate, filtered and desolvated to obtain 22.1g of light yellow solid, yield 73.3%.

Reference： [1]Current Patent Assignee: NANKAI UNIVERSITY - CN111689927, 2020, A Location in patent: Paragraph 0052-0053

16
[ 1201633-72-8 ]
[ 112257-19-9 ]
tert-butyl methyl(2-(methyl(7-oxo-4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)amino)ethyl)carbamate [ No CAS ]