[ CAS No. 1241377-74-1 ]

Name: 1241377-74-1|6-Bromonaphthalene-1,2-diamine|95%
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Product Details of [ 1241377-74-1 ]

CAS No. :	1241377-74-1	MDL No. :	MFCD21496290
Formula :	C₁₀H₉BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	237.10 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 1241377-74-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P501-P261-P273-P272-P202-P201-P264-P280-P302+P352-P308+P313-P337+P313-P305+P351+P338-P362+P364-P333+P313-P405	UN#:	N/A
Hazard Statements:	H315-H319-H351	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1241377-74-1 ]

* 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.

Downstream synthetic route of [ 1241377-74-1 ]

[ 1241377-74-1 ] Synthesis Path-Downstream 1~12

1
6-bromo-naphthalene-1,2-diamine [ No CAS ]
[ 15761-39-4 ]
[ 1309945-26-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 9h;	6.F To a solution of Compound Int-6e (40.5 g, 171 mmol), iY-Boc-proline (45.0 g, 209 mmol) and N N-diisopropylethylamine (90 mL, 517 mmol) in anhydrous- MF (1 L) at 0 °C was added HATU (78 g, 205 mmol). The resulting reaction was warmed to room temperature then stirred at this temperature for 9 hours. Water (1.5 L) was added to the reaction mixture and the resulting solution was extracted with MTBE (3 x 1.5 L). The combined organic extracts were washed with brine (3 1 L), dried over Na2S0 filtered and concentrated in vacuo. The residue obtained was dissolved in MeOH (75 mL) and water (1.5 L) was added. The resulting heterogeneous mixture was allowed to stir vigorously for 2 hours, then filtered. The filter cake was washed with water (1 L) and dried in vacuo at 55 °C to provide Compound Int-6f as an off-white solid (66.5 g, 90%), which was-used without further purification. 1H NMR (DMSO-i¾) δ 9.4.5-9.42 (m, 1H), 8.12- 8.09 (m, 1H), 8.00 (s, 1H), 7.52-7.47 (m, 1H), 7.36-7.33 (m, 1H-), 7.19-7:08 (m, 1), 5.58 (s, 1H), 5.45 (s, 1H), 4.35-4.21 (m, 1H), 3.45-3.31 (m, 2H), 2.33-2.13 (m, IE), 2.0-1.75 (m, 3H), 1.46-1.38 (ms 9H).
90%	With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 9h;
	With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 9h;	1.F Step F - Preparation of Compound IFIFTo a solution of compound IE (40.5 g, 171 mmol),. ;V-Boc-proiine (45.0 g, 209 mmol) and N,N-diisopropylethylamine (90 mL, 517 mmol) in anhydrous DMF (1 L) at 0 °C was added HATU (78 g, 205 mmol). The resulting mixture was wanned to room temperature then stirred at this temperature for 9 hours. Water (1.5 L) was added to the reaction mixture and the resulting aqueous solution was extracted with MTBE (3 χ 1.5 L). The combined organics were washed with brine (3 x 1 L), dried over Na2S04, filtered and concentrated in vacuo. The resulting residue was dissolved in MeOH (75 mL) and water (1.5 L) was added. The resulting heterogeneous mixture was stirred vigorously for 2 hours and filtered. The filter cake was washed with water (1 L) and dried in vacuo at 55 °C to provide Compound IF as an off-white solid (66.5 g, 90%). 1H NMR (DMSO-^) δ 9.45-9.42 (m, 1H), 8.12-8.09 (m, 1H), 8.00 (s, 1H), 7.52-7.47 (m, 1H), 7.36-7.33 (m, 1H), 7.19-7.08 (m, 1H), 5.58 (s, 1H), 5.45 (s, 1R), 4.35-4.21- (m, 1H), 3.45-3.31 (m, 2H), 2.33-2.13 (m, 1H), 2.0-1.75 (m, 3H), 1.46-1.38 (m, 9H-).

	With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 9h;	17.F Step F - Syntheses of Intermediate Compound Int-17f Step F - Syntheses of Intermediate Compound Int-17f (0338) (0339) To a solution of Compound Int-17e (40.5 g, 171 mmol), N-Boc-proline (45.0 g, 209 mmol) and diisopropylethylamine (90 mL, 517 mmol) in anhydrous DMF (1 L) at 0 °C was added HATU (78 g, 205 mmol). The resulting reaction was warmed to room temperature then allowed to stir at this temperature for 9 hours. Water (1.5 L) was added to the reaction mixture and the resulting solution was extracted with MTBE (3 × 1.5 L). The combined organic extracts were washed with brine (3 × 1 L), dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue was dissolved in MeOH (75 mL) and water (1.5 L) was added. The resulting heterogeneous mixture was allowed to stir vigorously for 2 hours, then filtered. The filter cake was washed with water (1 L) and dried in vacuo at 55 °C to provide Compound Int-17f as an off-white solid (66.5 g, 90%), which was used without further purification. 1H NMR (DMSO-d6) δ 9.45-9.42 (m, 1H), 8.12-8.09 (m, 1H), 8.00 (s, 1H), 7.52-7.47 (m, 1H), 7.36-7.33 (m, 1H), 7.19-7.08 (m, 1H), 5.58 (s, 1H), 5.45 (s, 1H), 4.35-4.21 (m, 1H), 3.45-3.31 (m, 2H), 2.33-2.13 (m, 1H), 2.0-1.75 (m, 3H), 1.46-1.38 (m, 9H).
	Stage #1: 1-(tert-butoxycarbonyl)-L-proline With chloroformic acid ethyl ester; triethylamine In dichloromethane at -10℃; for 0.166667h; Stage #2: 6-bromo-naphthalene-1,2-diamine In dichloromethane at -5 - 20℃; for 2h;	6.5 Synthesis of compound 7-6A To a solution of (S) -1- (tert-butoxycarbonyl) pyrrolidine-2-carboxylic acid (9.06 g , 42.17 mmol, 1.00 eq) , ethyl carbonochloridate (4.58 g, 42.17 g, 1.00 eq) in DCM (100 mL) was added dropwise Et3N (8.8 mL, 63.26 mmol, 1.50 eq) at -10 . After the addition, the mixture was maintained at -10 for 10 min, then filtered. The filter cake was washed with DCM (10 mL ×2) , and the filtrate was collected and reserved for the later use. To a solution of compound 7-5A (10 g, 42.17 mmol, 1.00 eq) in DCM (80 mL) was added dropwise the filtrate at -5 . After the addition, the resulting mixture was stirrd at rt for 2 h. After the reaction was completed, 100 mL of water was added, then the mixture was partitioned. The aqueous layer was extracted with DCM (50 mL × 2) . The combined organic layers were dried and concentrated to give the crude product as a brown black solid (18.00 g, 95.18) . 1H NMR (400 MHz, CDCl3) : δ 7.90 (s, 1H) , 7.65 (d, J 9.0 Hz, 1H) , 7.47 (d, J 8.1 Hz, 1H) , 7.40 (d, J 8.6 Hz, 1H) , 7.16 (d, J 8.6 Hz, 1H) , 4.61 -4.34 (m, 3H) , 4.00 (d, J 5.1 Hz, 1H) , 2.43 (s, 2H) , 2.13 (dd, J 12.8, 7.1 Hz, 2H) , 1.90 -1.63 (m, 2H) , 1.54 (s, 9H) ppm MS-ESI, m/z: 434.2 [M+H]+.

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2011/87740, 2011, A1 Location in patent: Page/Page column 76; 77
[2]Yu, Wensheng; Vibulbhan, Bancha; Rosenblum, Stuart B.; Martin, Gregory S.; Vellekoop, A. Samuel; Holst, Christian L.; Coburn, Craig A.; Wong, Michael; Selyutin, Oleg; Ji, Tao; Zhong, Bin; Hu, Bin; Chen, Lei; Dwyer, Michael P.; Jiang, Yueheng; Nair, Anilkumar G.; Tong, Ling; Zeng, Qingbei; Agrawal, Sony; Carr, Donna; Rokosz, Laura; Liu, Rong; Curry, Stephanie; McMonagle, Patricia; Ingravallo, Paul; Lahser, Fred; Asante-Appiah, Ernest; Fells, James; Kozlowski, Joseph A. [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3793 - 3799]
[3]Current Patent Assignee: MERCK & CO INC - WO2011/66241, 2011, A1 Location in patent: Page/Page column 110
[4]Current Patent Assignee: MERCK & CO INC - EP2545060, 2015, B1 Location in patent: Paragraph 0338; 0339
[5]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2016/141890, 2016, A1 Location in patent: Paragraph 00248; 00253

2
[ 71590-32-4 ]
[ 1241377-74-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: nitric acid; acetic anhydride / acetic acid / 6.5 h / 0 - 20 °C 2: hydrogenchloride; methanol / 6 h / 75 °C 3: water; iron / ammonium chloride / tetrahydrofuran / 3 h / 60 °C
	Multi-step reaction with 3 steps 1: acetic anhydride; acetic acid; nitric acid / 6.5 h / 0 - 20 °C 2: hydrogenchloride; water / methanol / 6 h / 75 °C 3: ammonium chloride; iron / water; tetrahydrofuran / 3 h / 60 °C
	Multi-step reaction with 3 steps 1: nitric acid / acetic acid / 6.5 h / 0 - 20 °C 2: hydrogenchloride / methanol; water / 6 h / 75 °C 3: iron; ammonium chloride / water; tetrahydrofuran / 3 h / 60 °C

	Multi-step reaction with 3 steps 1: potassium nitrate; sulfuric acid / acetic acid / 7 h / 20 - 30 °C 2: hydrogenchloride / tetrahydrofuran / 7 h / 80 °C 3: sodium carbonate; sodium dithionite / 1,4-dioxane / 5 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1: nitric acid; acetic anhydride / acetic acid / 4.5 h / 0 - 20 °C 2: hydrogenchloride / methanol; water / 6 h / 75 °C 3: iron; ammonium chloride / tetrahydrofuran; water / 3 h / 60 °C
	Multi-step reaction with 3 steps 1: nitric acid / acetic anhydride; acetic acid / 11 h / 35 - 45 °C / Industrial scale 2: ammonium chloride; water; iron / tetrahydrofuran / 6 h / 55 - 65 °C / Industrial scale 3: hydrogenchloride / methanol / 5 h / 55 - 65 °C / Industrial scale

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2011/66241, 2011, A1
[2]Current Patent Assignee: MERCK & CO INC - EP2545060, 2015, B1
[3]Yu, Wensheng; Vibulbhan, Bancha; Rosenblum, Stuart B.; Martin, Gregory S.; Vellekoop, A. Samuel; Holst, Christian L.; Coburn, Craig A.; Wong, Michael; Selyutin, Oleg; Ji, Tao; Zhong, Bin; Hu, Bin; Chen, Lei; Dwyer, Michael P.; Jiang, Yueheng; Nair, Anilkumar G.; Tong, Ling; Zeng, Qingbei; Agrawal, Sony; Carr, Donna; Rokosz, Laura; Liu, Rong; Curry, Stephanie; McMonagle, Patricia; Ingravallo, Paul; Lahser, Fred; Asante-Appiah, Ernest; Fells, James; Kozlowski, Joseph A. [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3793 - 3799]
[4]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2016/141890, 2016, A1
[5]Current Patent Assignee: MERCK & CO INC - WO2011/87740, 2011, A1
[6]Current Patent Assignee: NANJING HUAGUAN BIOTECHNOLOGY - CN112679365, 2021, A

3
[ 1241377-74-1 ]
[ 1180668-98-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 9 h / 0 - 20 °C 2.1: acetic acid / 1 h / 60 °C 2.2: pH 7
	Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 9 h / 0 - 20 °C 2.1: acetic acid / 1 h / 60 °C 2.2: 20 °C / pH 8

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2011/66241, 2011, A1
[2]Current Patent Assignee: MERCK & CO INC - WO2011/87740, 2011, A1

4
[ 1241377-74-1 ]
[ 1309945-27-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 9 h / 0 - 20 °C 2.1: acetic acid / 1 h / 60 °C 2.2: pH 7 3.1: potassium acetate / tricyclohexylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ / 1,4-dioxane / 4 h / 100 °C
	Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 9 h / 0 - 20 °C 2.1: acetic acid / 1 h / 60 °C 2.2: 20 °C / pH 8 3.1: potassium acetate / bis(dibenzylideneacetone)-palladium⁽⁰⁾; tricyclohexylphosphine / 1,4-dioxane / 4 h / 100 °C

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2011/66241, 2011, A1
[2]Current Patent Assignee: MERCK & CO INC - WO2011/87740, 2011, A1

5
[ 1241377-74-1 ]
[ 1315625-52-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 9 h / 0 - 20 °C 2.1: acetic acid / 1 h / 60 °C 2.2: 20 °C / pH 8 3.1: potassium acetate / bis(dibenzylideneacetone)-palladium⁽⁰⁾; tricyclohexylphosphine / 1,4-dioxane / 4 h / 100 °C 4.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 15 h / 100 °C