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[ CAS No. 1420477-60-6 ] {[proInfo.proName]}

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Chemical Structure| 1420477-60-6
Chemical Structure| 1420477-60-6
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Product Details of [ 1420477-60-6 ]

CAS No. :1420477-60-6 MDL No. :MFCD29472294
Formula : C26H23N7O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WDENQIQQYWYTPO-IBGZPJMESA-N
M.W : 465.51 Pubchem ID :71226662
Synonyms :
ACP-196

Safety of [ 1420477-60-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P260-P314-P501 UN#:N/A
Hazard Statements:H373 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1420477-60-6 ]

* 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 [ 1420477-60-6 ]
  • Downstream synthetic route of [ 1420477-60-6 ]

[ 1420477-60-6 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 590-93-2 ]
  • [ 1420477-60-6 ]
YieldReaction ConditionsOperation in experiment
78% With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25 - 30℃; 10 (50.88 g, 100 mmol) and N,N-dimethylformamide (254 mL) were added to a three-neck flask.Stir well and cool to 0~5 °C.Add butynoic acid (9.25 g, 110 mmol),Add EDCI (23.00g, 120mmol),N-methylmorpholine (40.46 g, 400 mmol) was added dropwise.After the addition, the reaction is carried out at 25 to 30 ° C for 6 to 8 hours.At the end of the reaction, water (254 mL) was added.Extracted 3 times with dichloromethane (127 mL),The combined organic phase 10percent sodium bicarbonate solution (127 mL) was washed once.Wash twice with saturated saline (127 mL),Dry over anhydrous sodium sulfate,After concentration, beat with isopropyl alcohol petroleum ether mixed solvent,filter,The product was dried (36.31 g, 78percent).
Reference: [1] Patent: CN108250186, 2018, A, . Location in patent: Paragraph 0086; 087; 0088
  • 2
  • [ 590-93-2 ]
  • [ 1420478-90-5 ]
  • [ 1420477-60-6 ]
YieldReaction ConditionsOperation in experiment
18% With triethylamine; HATU In dichloromethane at 20℃; for 0.5 h; (S)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N- (pyridin-2-yl)benzamide was made from (S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1 ,5- a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide and 2-butynoic acid as follows. To a solution of (S)- 4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide (19.7 mg, 0.049 mmol), triethylamine (20 mg, 0.197 mmol, 0.027 mL) 2-butynoic acid (4.12 mg, 0.049 mmol) in dichloromethane (2 mL) was added HATU (18.75 mg, 0.049 mmol). The mixture was stirred for 30 min at room temperature. The mixture was washed with water dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative HPLC. Fractions containing product were collected and reduced to dryness to afford the title compound (10.5 mg, 18.0percent).
18% With triethylamine; HATU In dichloromethane at 20℃; for 0.5 h; (S)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N- (pyridin-2-yl)benzamide was made from (S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1 ,5- a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide and 2-butynoic acid as follows. To a solution of (S)- 4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide (19.7 mg, 0.049 mmol), triethylamine (20 mg, 0.197 mmol, 0.027 mL) 2-butynoic acid (4.12 mg, 0.049 mmol) in dichloromethane (2 mL) was added HATU (18.75 mg, 0.049 mmol). The mixture was stirred for 30 min at room temperature. The mixture was washed with water dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative HPLC. Fractions containing product were collected and reduced to dryness to afford the title compound (10.5 mg, 18.0percent).
18% With triethylamine; HATU In dichloromethane at 20℃; for 0.5 h; (S)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N- (pyridin-2-yl)benzamide was made from (S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1 ,5- a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide and 2-butynoic acid as follows. To a solution of (S)- 4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide (19.7 mg, 0.049 mmol), triethylamine (20 mg, 0.197 mmol, 0.027 mL) 2-butynoic acid (4.12 mg, 0.049 mmol) in dichloromethane (2 mL) was added HATU (18.75 mg, 0.049 mmol). The mixture was stirred for 30 min at room temperature. The mixture was washed with water dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative HPLC. Fractions containing product were collected and reduced to dryness to afford the title compound (10.5 mg, 18.0percent).
Reference: [1] Patent: WO2016/24227, 2016, A1, . Location in patent: Paragraph 00205
[2] Patent: WO2016/24232, 2016, A1, . Location in patent: Paragraph 00504
[3] Patent: WO2016/24230, 2016, A1, . Location in patent: Paragraph 00472
  • 3
  • [ 1418307-18-2 ]
  • [ 1420477-60-6 ]
Reference: [1] Patent: WO2016/24227, 2016, A1,
[2] Patent: WO2016/24230, 2016, A1,
[3] Patent: WO2016/24232, 2016, A1,
[4] Patent: CN107522701, 2017, A,
  • 4
  • [ 1420478-88-1 ]
  • [ 1420477-60-6 ]
Reference: [1] Patent: WO2016/24227, 2016, A1,
[2] Patent: WO2016/24230, 2016, A1,
[3] Patent: WO2016/24232, 2016, A1,
[4] Patent: CN108250186, 2018, A,
  • 5
  • [ 1420478-89-2 ]
  • [ 1420477-60-6 ]
Reference: [1] Patent: WO2016/24227, 2016, A1,
[2] Patent: WO2016/24232, 2016, A1,
[3] Patent: WO2016/24230, 2016, A1,
[4] Patent: CN108250186, 2018, A,
  • 6
  • [ 1418307-17-1 ]
  • [ 1420477-60-6 ]
Reference: [1] Patent: WO2016/24227, 2016, A1,
[2] Patent: WO2016/24230, 2016, A1,
[3] Patent: WO2016/24232, 2016, A1,
  • 7
  • [ 1420478-87-0 ]
  • [ 1420477-60-6 ]
Reference: [1] Patent: WO2016/24227, 2016, A1,
[2] Patent: WO2016/24230, 2016, A1,
[3] Patent: WO2016/24232, 2016, A1,
  • 8
  • [ 180516-87-4 ]
  • [ 1420477-60-6 ]
Reference: [1] Patent: CN108250186, 2018, A,
[2] Patent: CN108250186, 2018, A,
  • 9
  • [ 504-29-0 ]
  • [ 1420477-60-6 ]
Reference: [1] Patent: CN108250186, 2018, A,
[2] Patent: CN108250186, 2018, A,
  • 10
  • [ 121246-96-6 ]
  • [ 1420477-60-6 ]
Reference: [1] Patent: CN107056786, 2017, A,
  • 11
  • [ 1333433-59-2 ]
  • [ 1420477-60-6 ]
Reference: [1] Patent: CN108250186, 2018, A,
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