[ CAS No. 139481-38-2 ] {[proInfo.proName]}

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Quality Control of [ 139481-38-2 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 139481-38-2 ]

CAS No. :	139481-38-2	MDL No. :
Formula :	C₂₇H₂₅N₃O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	487.50	Pubchem ID :	-
Synonyms :

Safety of [ 139481-38-2 ]

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Application In Synthesis of [ 139481-38-2 ]

* 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 [ 139481-38-2 ]
Downstream synthetic route of [ 139481-38-2 ]

[ 139481-38-2 ] Synthesis Path-Upstream 1~5

1
[ 139481-38-2 ]
[ 136285-69-3 ]

Reference： [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195

2
[ 139481-38-2 ]
[ 139481-28-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With hydrogenchloride In methanol; water for 5.5 h; Heating / reflux; Industry scale	30.1 g of methyl 2-tert-butoxycarbonylamino-3-nitrobenzoate [BAN], 40.8 g of potassium carbonate and 160 ml of acetonitrile were added to the acetonitrile solution in which unreacted 2-(4-methylphenyl)benzonitrile [MPB] and 2-(4,4-dibromomethylphenyl)benzonitrile as an analogue of BMB were contaminated, and the reaction was allowed to proceed at about 82 °C for about 5 hours under stirring.. After cooling to room temperature, the precipitated crystals were filtered off, and the filtrate was concentrated to give methyl 2-[N-t-butoxycarbonyl-N-[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate [BBN].. The concentrated material was dissolved in 190 g of methanol, and 106 g of concentrated hydrochloric acid was added dropwise thereto.. The resulting solution was heated to a reflux temperature over 2 hours, and stirred for 2 hours under reflux, whereby, the reaction was allowed to proceed.. The reaction solution was cooled, and precipitated crystals were collected by filteration and dried to give 35.1 g of methyl 2-[N-(2'-cyanobiphenyl-4-yl)methylamino]-3-nitrobenzoate [MBN] (yield relative to 2-(4-methylphenyl)benzonitrile [MPB] was 76.1 percent). The concentrate (methyl 2-[N-t-butoxycarbonyl-N-[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate [BBN]) obtained in Reference Example 4(2) and methanol (3200 L) were mixed, and 35percent concentrated hydrochloric acid (1050 L) was added at 30°C or lower over about 4 hours.. The mixture was heated to a reflux temperature (67 to 69°C) at a temperature rising rate of 10°C/hour or lower, and stirred under reflux for about 1.5 hours.. The reaction solution was cooled, methanol (800 L) was added thereto, and the solution was stirred at 3 to 10 °C for about 1 hour.. The precipitated crystals ware separated, and washed with methanol, followed by drying to give methyl 2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate [MBN] (407 kg; yield relative to MPB was 75percent). mp. 140 to 141°C 1H-NMR(200MHz, DMSO-d6)δ: 3.84(3H,s), 4.26(2H,m), 6.86(1H,t), 7.46(2H,d), 7.54-7.65(4H,m), 7.79(1H,d), 7.95(1H,dd), 8.05-8.11(2H,m), 8.67(1H,t)

Reference： [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
[2] Patent: EP1420016, 2004, A1, . Location in patent: Page 16-17; 18

3
[ 139481-38-2 ]
[ 139481-44-0 ]

Reference： [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195

4
[ 139481-38-2 ]
[ 139481-69-9 ]

Reference： [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195

5
[ 139481-38-2 ]
[ 139481-59-7 ]

Reference： [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195

[ 139481-38-2 ] Synthesis Path-Downstream 1~9

1
[ 57113-90-3 ]
[ 114772-54-2 ]
[ 139481-38-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; at 80 - 85℃; for 5h;Heating / reflux; Industry scale;	methyl 2-t-butoxycarbonylamino-3-nitrobenzoate [BAN] obtained in Reference Example 3 (354 kg), a solution of 4-(2-bromomethylphenyl)benzonitrile [BMB] in acetonitrile obtained in Reference Example 4 (1), and anhydrous potassium carbonate (475 kg) were added to acetonitrile (1600 kg), and the mixture was heated (80 to 85 C) under reflux for about 5 hours.. The reaction solution was cooled, and the insoluble were separated and washed with acetonitrile (320 kg).. The filtrated washing was concentrated under reduced pressure to give concentrate of methyl 2-[N-t-butoxycarbonyl-N-[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate [BBN].

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2182 - 2195
[2]Patent: EP1420016,2004,A1 .Location in patent: Page 18

2
[ 139481-38-2 ]
[ 139481-28-0 ]

Yield	Reaction Conditions	Operation in experiment
75 - 76.1%	With hydrogenchloride; In methanol; water; for 5.5h;Heating / reflux; Industry scale;	30.1 g of methyl 2-tert-butoxycarbonylamino-3-nitrobenzoate [BAN], 40.8 g of potassium carbonate and 160 ml of acetonitrile were added to the acetonitrile solution in which unreacted 2-(4-methylphenyl)benzonitrile [MPB] and 2-(4,4-dibromomethylphenyl)benzonitrile as an analogue of BMB were contaminated, and the reaction was allowed to proceed at about 82 C for about 5 hours under stirring.. After cooling to room temperature, the precipitated crystals were filtered off, and the filtrate was concentrated to give methyl 2-[N-t-butoxycarbonyl-N-[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate [BBN].. The concentrated material was dissolved in 190 g of methanol, and 106 g of concentrated hydrochloric acid was added dropwise thereto.. The resulting solution was heated to a reflux temperature over 2 hours, and stirred for 2 hours under reflux, whereby, the reaction was allowed to proceed.. The reaction solution was cooled, and precipitated crystals were collected by filteration and dried to give 35.1 g of methyl 2-[N-(2'-cyanobiphenyl-4-yl)methylamino]-3-nitrobenzoate [MBN] (yield relative to 2-(4-methylphenyl)benzonitrile [MPB] was 76.1 %). The concentrate (methyl 2-[N-t-butoxycarbonyl-N-[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate [BBN]) obtained in Reference Example 4(2) and methanol (3200 L) were mixed, and 35% concentrated hydrochloric acid (1050 L) was added at 30C or lower over about 4 hours.. The mixture was heated to a reflux temperature (67 to 69C) at a temperature rising rate of 10C/hour or lower, and stirred under reflux for about 1.5 hours.. The reaction solution was cooled, methanol (800 L) was added thereto, and the solution was stirred at 3 to 10 C for about 1 hour.. The precipitated crystals ware separated, and washed with methanol, followed by drying to give methyl 2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate [MBN] (407 kg; yield relative to MPB was 75%). mp. 140 to 141C 1H-NMR(200MHz, DMSO-d6)delta: 3.84(3H,s), 4.26(2H,m), 6.86(1H,t), 7.46(2H,d), 7.54-7.65(4H,m), 7.79(1H,d), 7.95(1H,dd), 8.05-8.11(2H,m), 8.67(1H,t)

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2182 - 2195
[2]Patent: EP1420016,2004,A1 .Location in patent: Page 16-17; 18

3
[ 21606-04-2 ]
[ 139481-38-2 ]