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Chemistry
Heterocyclic Building Blocks
Quinolines
Verubulin HCl
Chemistry
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Heterocyclic Building Blocks
Organic Building Blocks Cell Cycle
Quinolines
Quinazolines Amines Microtubule/Tubulin

[ CAS No. 917369-31-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 917369-31-4
Chemical Structure| 917369-31-4
Structure of 917369-31-4 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 917369-31-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
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Product Details of [ 917369-31-4 ]

CAS No. :917369-31-4 MDL No. :MFCD22741413
Formula : C17H18ClN3O Boiling Point : -
Linear Structure Formula :- InChI Key :VYUWDIKZJLOZJL-UHFFFAOYSA-N
M.W : 315.80 Pubchem ID :11638255
Synonyms :
MPC-6827 hydrochloride;Verubulin hydrochloride;MPC-6827;Verubulin;MPC-6827 (hydrochloride)

Safety of [ 917369-31-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 917369-31-4 ]

* 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 [ 917369-31-4 ]

[ 917369-31-4 ] Synthesis Path-Downstream   1~5

YieldReaction ConditionsOperation in experiment
71%
71%
71%
  • 2
  • [ 917369-31-4 ]
  • [ 827031-26-5 ]
YieldReaction ConditionsOperation in experiment
6% With boron tribromide In dichloromethane at -78 - 10℃; Inert atmosphere;
With boron tribromide In dichloromethane at -78 - 10℃; for 1.5h; 93 (4-HYDROXY-PHENYL)- (2-METHYL-QUINAZOLIN-4-YL)-METHYL-AMINE To a solution of (4-METHOXY-PHENYL)- (2-METHYL-QUINAZOLIN-4-YL)-METHYL- amine hydrochloride salt (106 mg, 0.336 mmol) in dichloromethane (10 mL) at-78 °C was added slowly boron tribromide (1M in CH2CI2, 0.75 mL) under argon. The cold bath was removed and the reaction mixture was allowed to warm up slowly to 10 °C in 1.5 h. The reaction mixture was quenched with water (10 mL), basified with 2NNAOH to pH = 10, and extracted with EtOAc (2X25 mL). The EtOAc extracts were dried and evaporated to give a light brown residue. The crude was purified by column chromatography (SI02, EtOAc: hexanes/15-50%) to give the product as a white solid, which was further purified by recrystallization from MeOH : H NMR (ACETONE-D6) 8.74 (s, 1H), 7.75 (m, 1H), 7.67 (m, 1H), 7.20-7. 18 (m, 3H), 7.12 (m, 1H), 7.04-6. 99 (m, 2H), 3.64 (s, 3H), 2.79 (s, 3H).
Reference： [1]Location in patent: experimental part Sirisoma, Nilantha; Pervin, Azra; Zhang, Hong; Jiang, Songchun; Willardsen, J. Adam; Anderson, Mark B.; Mather, Gary; Pleiman, Christopher M.; Kasibhatla, Shailaja; Tseng, Ben; Drewe, John; Cai, Sui Xiong [Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2341 - 2351]
[2]Current Patent Assignee: MYREXIS, INC.; IMMUNE PHARMACEUTICALS INC; MYRIAD GENETICS INC - WO2005/3100, 2005, A2 Location in patent: Page 206
  • 3
  • [ 6484-24-8 ]
  • [ 5961-59-1 ]
  • Verubulin hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With hydrogenchloride In water; isopropyl alcohol at 20℃;
71% With hydrogenchloride In water 1.b; 1 b) (4-Methoxy-phenyl)-methyl-(2-methyl-quinazolin-4-yl)-amine hydrochloride:The title compound was prepared from 4-chloro-2-methyl-quinazoline (2.31 g, 12.9 mmol) and (4-methoxy phenyl)-methyl-amine (2.0 g, 14.6 mmol) by a procedure similar to example Ib and was isolated as solids (2.90 g, 9.18 mmol, 71%). 1H NMR (CDCl3): 8.53 (dd, IH, J= 0.6, 8.1), 7.7 (ddd, IH, J= 1.2, 7.2, 8.4), 7.22 (m, 2H), 7.13 (ddd, IH, J = 1.2, 7.2, 8.7), 7.05 (m, 2H), 6.76 (d, IH, J = 8.7), 3.91 (s, 3H), 3.78 (s, 3H), 2.96 (s, 3H).
71% 1.b The title compound was prepared from 4-chloro-2-methyl-quinazoline (2.31 g, 12.9 mmol) and (4-methoxy phenyl)-methyl-amine (2.0 g, 14.6 mmol) by a procedure similar to example Ib and was isolated as solids (2.90 g, 9.18 mmol, 71%). 1H NMR (CDCl3): 8.53 (dd, IH, J= 0.6, 8.1), 7.7 (ddd, IH, J= 1.2, 7.2, 8.4), 7.22 (m, 2H), 7.13 (ddd, IH, J = 1.2, 7.2, 8.7), 7.05 (m, 2H), 6.76 (d, IH, J = 8.7), 3.91 (s, 3H), 3.78 (s, 3H), 2.96 (s, 3H).
71% With hydrogenchloride In water 1 The title compound was prepared from 4-chloro-2-methyl-quinazoline (2.31 g, 12.9 mmol) and (4-methoxy phenyl)-methyl-amine (2.0 g, 14.6 mmol) by a procedure similar to example Ib and was isolated as solids (2.90 g, 9.18 mmol, 71%). 1H NMR (CDCl3): 8.53 (dd, IH, J= 0.6, 8.1), 7.7 (ddd, IH, J= 1.2, 7.2, 8.4), 7.22 (m, 2H), 7.13 (ddd, IH, J = 1.2, 7.2, 8.7), 7.05 (m, 2H), 6.76 (d, IH, J = 8.7), 3.91 (s, 3H), 3.78 (s, 3H), 2.96 (s, 3H).

Reference： [1]Location in patent: experimental part Sirisoma, Nilantha; Pervin, Azra; Zhang, Hong; Jiang, Songchun; Willardsen, J. Adam; Anderson, Mark B.; Mather, Gary; Pleiman, Christopher M.; Kasibhatla, Shailaja; Tseng, Ben; Drewe, John; Cai, Sui Xiong [Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2341 - 2351]
[2]Current Patent Assignee: MYREXIS, INC. - WO2008/124822, 2008, A1 Location in patent: Page/Page column 10; 13
[3]Current Patent Assignee: MYREXIS, INC. - WO2008/124823, 2008, A1 Location in patent: Page/Page column 11
[4]Current Patent Assignee: MYREXIS, INC. - WO2008/124828, 2008, A1 Location in patent: Page/Page column 9; 11-12
  • 4
  • [ 1769-24-0 ]
  • [ 917369-31-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trichlorophosphate / 3 h / 120 °C 2: hydrogenchloride / water
Reference： [1]Current Patent Assignee: MYREXIS, INC. - WO2008/124822, 2008, A1
  • 5
  • [ 134-20-3 ]
  • [ 917369-31-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogenchloride 2: trichlorophosphate / 3 h / 120 °C 3: hydrogenchloride / water
Reference： [1]Current Patent Assignee: MYREXIS, INC. - WO2008/124822, 2008, A1

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[ 917369-31-4 ]

Chemical Structure| 827031-83-4

A799965[ 827031-83-4 ]

N-(4-Methoxyphenyl)-N,2-dimethylquinazolin-4-amine

Reason: Free-salt