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[ CAS No. 1377049-84-7 ]

{[proInfo.proName]} (Synonyms:GS-5816) ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1377049-84-7
Chemical Structure| 1377049-84-7
Structure of 1377049-84-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1377049-84-7 ]

CAS No. :1377049-84-7 MDL No. :MFCD28411371
Formula : C49H54N8O8 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :883.00 g/mol Pubchem ID :67683363
Synonyms :

1. Velpatasvir

Calculated chemistry of of [ 1377049-84-7 ]

Physicochemical Properties

Num. heavy atoms : 65
Num. arom. heavy atoms : 30
Fraction Csp3 : 0.39
Num. rotatable bonds : 17
Num. H-bond acceptors : 10.0
Num. H-bond donors : 4.0
Molar Refractivity : 251.54
TPSA : 193.1 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.9
Log Po/w (XLOGP3) : 6.16
Log Po/w (WLOGP) : 5.84
Log Po/w (MLOGP) : 1.7
Log Po/w (SILICOS-IT) : 6.28
Consensus Log Po/w : 4.98

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 2.0
Egan : 1.0
Muegge : 5.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -8.41
Solubility : 0.0000034 mg/ml ; 0.0000000038 mol/l
Class : Poorly soluble
Log S (Ali) : -10.0
Solubility : 0.0000000886 mg/ml ; 0.0000000001 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -12.21
Solubility : 0.0000000005 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 7.49

Safety of [ 1377049-84-7 ]

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 [ 1377049-84-7 ]

* 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 [ 1377049-84-7 ]

[ 1377049-84-7 ] Synthesis Path-Downstream   1~31

  • 1
  • [ 1378391-39-9 ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 2: caesium carbonate / 20 h / 50 °C 3: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 4: manganese(IV) oxide / dichloromethane / 13 h 5: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 6: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C
Multi-step reaction with 5 steps 1.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 2.1: caesium carbonate / 2-methyltetrahydrofuran / 20 h / 50 °C 3.1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 4.1: manganese(IV) oxide / dichloromethane / 13 h 5.1: hydrogenchloride / ethanol / 3 h / 50 °C 5.2: 2 h / 20 °C
Multi-step reaction with 9 steps 1.1: hydrogenchloride / water; Isopropyl acetate / 60 - 65 °C / Industrial scale 2.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / N,N-dimethyl-formamide / 20 - 25 °C / Industrial scale 3.1: ammonium acetate / toluene / 20 h / 80 - 100 °C / Inert atmosphere; Industrial scale 4.1: tribromopyridine / methanol; dichloromethane / 3 h / 10 - 15 °C / Industrial scale 5.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 - 40 °C / Inert atmosphere; Industrial scale 6.1: ammonium acetate / toluene / 20 h / 80 - 100 °C / Inert atmosphere; Industrial scale 7.1: manganese(IV) oxide / dichloromethane / 10 - 20 °C / Inert atmosphere; Industrial scale 7.2: 60 °C / Industrial scale 8.1: trifluorormethanesulfonic acid / methanol / 60 - 65 °C / Industrial scale 9.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile / 1 h / 10 - 15 °C / Industrial scale 9.2: 0 - 15 °C / Industrial scale
  • 2
  • [ 1378391-42-4 ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: caesium carbonate / 20 h / 50 °C 2: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 3: manganese(IV) oxide / dichloromethane / 13 h 4: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 5: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C
Multi-step reaction with 4 steps 1.1: caesium carbonate / 2-methyltetrahydrofuran / 20 h / 50 °C 2.1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 3.1: manganese(IV) oxide / dichloromethane / 13 h 4.1: hydrogenchloride / ethanol / 3 h / 50 °C 4.2: 2 h / 20 °C
  • 3
  • [ 1378391-43-5 ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 2: manganese(IV) oxide / dichloromethane / 13 h 3: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 4: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C
Multi-step reaction with 3 steps 1.1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 2.1: manganese(IV) oxide / dichloromethane / 13 h 3.1: hydrogenchloride / ethanol / 3 h / 50 °C 3.2: 2 h / 20 °C
Multi-step reaction with 4 steps 1: hydrogenchloride / ethanol; water / 0 - 80 °C 2: ammonium formate / 2-methoxy-ethanol / 100 - 105 °C 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 30 - 35 °C 4: acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / tetrahydrofuran / 0 - 5 °C / Inert atmosphere
  • 4
  • [ 1378391-44-6 ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: manganese(IV) oxide / dichloromethane / 13 h 2: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 3: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C
Multi-step reaction with 2 steps 1.1: manganese(IV) oxide / dichloromethane / 13 h 2.1: hydrogenchloride / ethanol / 3 h / 50 °C 2.2: 2 h / 20 °C
Multi-step reaction with 3 steps 1.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 1.2: 4 h / 60 °C 2.1: ammonium hydroxide / dichloromethane; water / 0.17 h 3.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
  • 5
  • [ 1378391-45-7 ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C
Multi-step reaction with 2 steps 1: hydrogenchloride / dichloromethane; 1,4-dioxane; methanol / 2 h 2: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 1 h
Multi-step reaction with 2 steps 1: hydrogenchloride / dichloromethane; 1,4-dioxane; methanol / 2 h 2: 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h
  • 6
  • C39H45N7O5*(x)ClH [ No CAS ]
  • [ 50890-96-5 ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
65 mg With 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; PY Methyl {(2S)-l-[(2S,5S)-2-(9-{2-[(2S,4S)-l-{(2R)-2-[(methoxycarbonyl)amino]-2-phenylacetyl}-4- (methoxymethyl)pyrrolidin-2-yl]-lH-imidazol-5-yl}-l,ll- dihydroisochromeno[4',3':6,7]naphtho[l,2-d]imidazol-2-yl)-5-methylpyrrolidin-l-yl]-3-methyl- 1 -oxobutan-2-yl} carbamate A solution of tert-butyl (2S,4S)-2-[5-(2- {(2S,5S)-l -[N-(methoxycarbonyl)-L-valyl]-5- methylpyrrolidin-2-yl}-l,l l-dihydroisochromeno[4',3':6,7]naphtho[l,2-d]imidazol-9-yl)-lH- imidazol-2-yl]-4-(methoxymethyl)pyrrolidine-l -carboxylate (150 mg, 0.19 mmol) in 1.25 N HCI in EtOH (3 mL) was stirred overnight then heated to 50 °C for 3h. The reaction was concentrated and the crude material dissolved in DMF (2 mL). To this solution was added a solution of (R)-2- (methoxycarbonylamino)-2-phenylacetic acid (52 mg, 0.25 mmol) and COMU (90 mg, 0.21 mmol). To the resulting solution was added diisopropylethylamine (0.099 mL, 0.57 mmol). After stirring for 2h at room temperature, the reaction was quenched with IN HCI (0.200 mL) and purified by HPLC. After lyophilization, the TFA salt was dissolved in EtOAc and washed with saturated NaHCOs. The organic phase was dried over Na2S04 and concentrated. The free base was then dissolved in MeCN/H20 and lyophilized to afford methyl {(2S)-l -[(2S,5S)-2-(9- {2-[(2S,4S)-l - {(2R)-2- [(methoxycarbonyl)amino]-2-phenylacetyl} -4-(methoxymethyl)pyrrolidin-2-yl]-lH-imidazol-5-yl} - l , l l -dihydroisochromeno[4',3':6,7]naphtho[l ,2-d]imidazol-2-yl)-5-methylpyrrolidin-l -yl]-3-methyl- l -oxobutan-2-yl} carbamate (65 mg, 39%). LCMS-ESI+: calculated for C49H54N808: 882.4; observed [M+l ]+: 884.1. Diagnostic peaks in NMR 'H NMR (CD3OD): 8.28 (s, 1H), 8.21 (s, 1H), 8.04 (s, 1H), 7.91 -7.01 (m, 10H), 3.62 (s, 3H), 3.34 (s, 3H), 3.23 (s, 3H), 1.56 (d, 3H), 1.03 (d, 3H), 0.94 (d, 3H).
  • 7
  • [ 487048-28-2 ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1.1: hydrogenchloride / 1,4-dioxane / 16 h / 20 °C 1.2: 12 h / 20 °C 2.1: water; sodium hydroxide / tert-Amyl alcohol / 5.25 h / 0 °C / Cooling with ice 3.1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 4.1: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 5.1: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 6.1: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 7.1: caesium carbonate / 4 h / 20 °C 8.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 9.1: caesium carbonate / 20 h / 50 °C 10.1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 11.1: manganese(IV) oxide / dichloromethane / 13 h 12.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 13.1: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C
Multi-step reaction with 11 steps 1.1: hydrogenchloride / 1,4-dioxane; methanol / 16 h / 20 °C 1.3: 12 h / 20 °C 2.1: sodium hydroxide; water / tetrahydrofuran / 5 h / 0 °C 3.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 3.2: 2 h / 0 °C 4.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / 3 h / 0 - 20 °C 5.1: water; lithium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C 6.1: caesium carbonate / 2-methyltetrahydrofuran / 4 h / 20 °C 7.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 8.1: caesium carbonate / 2-methyltetrahydrofuran / 20 h / 50 °C 9.1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 10.1: manganese(IV) oxide / dichloromethane / 13 h 11.1: hydrogenchloride / ethanol / 3 h / 50 °C 11.2: 2 h / 20 °C
  • 8
  • [ 1378388-30-7 ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1: water; sodium hydroxide / tert-Amyl alcohol / 5.25 h / 0 °C / Cooling with ice 2: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 3: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 4: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 5: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 6: caesium carbonate / 4 h / 20 °C 7: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 8: caesium carbonate / 20 h / 50 °C 9: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 10: manganese(IV) oxide / dichloromethane / 13 h 11: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 12: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C
Multi-step reaction with 10 steps 1.1: sodium hydroxide; water / tetrahydrofuran / 5 h / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 2.2: 2 h / 0 °C 3.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / 3 h / 0 - 20 °C 4.1: water; lithium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C 5.1: caesium carbonate / 2-methyltetrahydrofuran / 4 h / 20 °C 6.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 7.1: caesium carbonate / 2-methyltetrahydrofuran / 20 h / 50 °C 8.1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 9.1: manganese(IV) oxide / dichloromethane / 13 h 10.1: hydrogenchloride / ethanol / 3 h / 50 °C 10.2: 2 h / 20 °C
  • 9
  • [ 1378388-35-2 ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 4 h / 20 °C 6: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 7: caesium carbonate / 20 h / 50 °C 8: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 9: manganese(IV) oxide / dichloromethane / 13 h 10: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 11: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C
Multi-step reaction with 9 steps 1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / 3 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C 4.1: caesium carbonate / 2-methyltetrahydrofuran / 4 h / 20 °C 5.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 6.1: caesium carbonate / 2-methyltetrahydrofuran / 20 h / 50 °C 7.1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 8.1: manganese(IV) oxide / dichloromethane / 13 h 9.1: hydrogenchloride / ethanol / 3 h / 50 °C 9.2: 2 h / 20 °C
  • 10
  • [ 1194059-42-1 ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 2: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 3: caesium carbonate / 4 h / 20 °C 4: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 5: caesium carbonate / 20 h / 50 °C 6: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 7: manganese(IV) oxide / dichloromethane / 13 h 8: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 9: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C
Multi-step reaction with 8 steps 1.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / 3 h / 0 - 20 °C 2.1: water; lithium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C 3.1: caesium carbonate / 2-methyltetrahydrofuran / 4 h / 20 °C 4.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 5.1: caesium carbonate / 2-methyltetrahydrofuran / 20 h / 50 °C 6.1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 7.1: manganese(IV) oxide / dichloromethane / 13 h 8.1: hydrogenchloride / ethanol / 3 h / 50 °C 8.2: 2 h / 20 °C
  • 11
  • [ 1378393-23-7 ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 2: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 3: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 4: caesium carbonate / 4 h / 20 °C 5: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 6: caesium carbonate / 20 h / 50 °C 7: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 8: manganese(IV) oxide / dichloromethane / 13 h 9: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 10: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C
  • 12
  • [ 1378388-37-4 ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 2: caesium carbonate / 4 h / 20 °C 3: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 4: caesium carbonate / 20 h / 50 °C 5: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 6: manganese(IV) oxide / dichloromethane / 13 h 7: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 8: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C
Multi-step reaction with 7 steps 1.1: water; lithium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C 2.1: caesium carbonate / 2-methyltetrahydrofuran / 4 h / 20 °C 3.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 4.1: caesium carbonate / 2-methyltetrahydrofuran / 20 h / 50 °C 5.1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 6.1: manganese(IV) oxide / dichloromethane / 13 h 7.1: hydrogenchloride / ethanol / 3 h / 50 °C 7.2: 2 h / 20 °C
  • 14
  • [ 1378391-45-7 ]
  • [ 50890-96-5 ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
65 mg Stage #1: tert-butyl (2S,4S)-2-[5-(2-{(2S,5S)-1-[N-(methoxycarbonyl)-L-valyl]-5-methylpyrrolidin-2-yl}-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl)-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidine-1-carboxylate With hydrogenchloride In ethanol at 50℃; for 3h; Stage #2: (2R)-2-[(methoxycarbonyl)amino]-2-phenylacetic acid With 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; CY A solution of tert-butyl (2S,4S)-2-[5-(2-{(2S,5S)-1-[N-(methoxycarbonyl)-L-valyl]-5-methylpyrrolidin-2-yl}-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl)-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidine-1-carboxylate (150 mg, 0.19 mmol) in 1.25 N HCl in EtOH (3 mL) was stirred overnight then heated to 50° C. for 3 h. The reaction was concentrated and the crude material dissolved in DMF (2 mL). To this solution was added a solution of (R)-2-(methoxycarbonylamino)-2-phenylacetic acid (52 mg, 0.25 mmol) and COMU (90 mg, 0.21 mmol). To the resulting solution was added diisopropylethylamine (0.099 mL, 0.57 mmol). After stirring for 2 h at room temperature, the reaction was quenched with 1N HCl (0.200 mL) and purified by HPLC. After lyophilization, the TFA salt was dissolved in EtOAc and washed with saturated NaHCO3. The organic phase was dried over Na2SO4 and concentrated. The free base was then dissolved in MeCN/H2O and lyophilized to afford methyl {(2S)-1-[(2S,5S)-2-(9-{2-[(2S,4S)-1-{(2R)-2-[(methoxycarbonyl)amino]-2-phenylacetyl}-4-(methoxymethyl)pyrrolidin-2-yl]-1H-imidazol-5-yl}-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate (65 mg, 39%). LCMS-ESI+: calculated for C49H54N8O8: 882.4; observed [M+1]+: 884.1. Diagnostic peaks in NMR 1H NMR (CD3OD): 8.28 (s, 1H), 8.21 (s, 1H), 8.04 (s, 1H), 7.91-7.01 (m, 10H), 3.62 (s, 3H), 3.34 (s, 3H), 3.23 (s, 3H), 1.56 (d, 3H), 1.03 (d, 3H), 0.94 (d, 3H)
  • 15
  • [ 1377049-84-7 ]
  • methyl {(1R)-2-[(2S,4S)-2-(5-{2-[(2S,5S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-5-methylpyrrolidin-2-yl]-11-oxo-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl}-1H-imidazol-2-yl)-4-(methoxymethyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl}carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With pyridinium chlorochromate In dichloromethane at 20℃; for 120h; GK To a solution of methyl {(2S)-1-[(2S,5S)-2-(9-{2-[(2S,4S)-1-{(2R)-2-[(methoxycarbonyl)amino]-2-phenylacetyl}-4-(methoxymethyl)pyrrolidin-2-yl]-1H-imidazol-5-yl}-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate (0.19 g, 0.22 mmol) in CH2Cl2 (3 mL) was added pyridinium chlorochromate (0.48 g, 2.21 mmol). The resulting slurry was stirred at room temperature for 5 days. The reaction was diluted with MeOH and filtered. The filtrate was diluted with CH2Cl2 and washed with water and aqueous sodium bicarbonate (saturated). The aqueous layers were backextracted with CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude oil was purified by reverse phase HPLC (Gemini, 10→55% MeCN/H2O (0.1% TFA)). The desired fractions were combined and concentrated under reduced pressure to remove volatile organics. The addition of aqueous sodium bicarbonate with stirring resulted in precipitation of a white solid. The precipitate was filtered through a membrane filter and washed with water. Drying under reduced pressure afforded methyl {(1R)-2-[(2S,4S)-2-(5-{2-[(2S,5S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-5-methylpyrrolidin-2-yl]-11-oxo-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl}-1H-imidazol-2-yl)-4-(methoxymethyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl}carbamate (0.08 g, 39%). LCMS-ESI+: calc'd for C49H52N8O9: 896.39 (M+); Found: 897.72 (M+H+).
  • 16
  • C34H33NO8 [ No CAS ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: ammonium acetate / 2-methoxy-ethanol; toluene / 16 - 90 °C 2.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 3 h / 20 - 25 °C 3.1: potassium carbonate / tetrahydrofuran / 16 - 45 °C 4.1: ammonium acetate / 2-methoxy-ethanol; toluene / 90 - 95 °C 5.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 5.2: 16 h / 20 °C 5.3: 4 h / 60 °C 6.1: ammonium hydroxide / dichloromethane; water / 0.17 h 7.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
  • 17
  • C31H35N3O5 [ No CAS ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 3 h / 20 - 25 °C 1.2: 0.5 h 1.3: 0.17 h 2.1: potassium carbonate / tetrahydrofuran / 16 - 45 °C 3.1: ammonium acetate / 2-methoxy-ethanol; toluene / 90 - 95 °C 4.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 4.2: 4 h / 60 °C 5.1: ammonium hydroxide / dichloromethane; water / 0.17 h 6.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
Multi-step reaction with 6 steps 1.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 3 h / 20 - 25 °C 2.1: potassium carbonate / tetrahydrofuran / 16 - 45 °C 3.1: ammonium acetate / 2-methoxy-ethanol; toluene / 90 - 95 °C 4.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 4.2: 4 h / 60 °C 5.1: ammonium hydroxide / dichloromethane; water / 0.17 h 6.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
  • 18
  • C34H33N3O5 [ No CAS ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 3 h / 20 - 25 °C 2.1: potassium carbonate / tetrahydrofuran / 16 - 45 °C 3.1: ammonium acetate / 2-methoxy-ethanol; toluene / 90 - 95 °C 4.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 4.2: 16 h / 20 °C 4.3: 4 h / 60 °C 5.1: ammonium hydroxide / dichloromethane; water / 0.17 h 6.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
  • 19
  • C31H34BrN3O5 [ No CAS ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / tetrahydrofuran / 16 - 45 °C 2.1: ammonium acetate / 2-methoxy-ethanol; toluene / 90 - 95 °C 3.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 3.2: 4 h / 60 °C 4.1: ammonium hydroxide / dichloromethane; water / 0.17 h 5.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
  • 20
  • C34H32BrN3O5 [ No CAS ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / tetrahydrofuran / 16 - 45 °C 2.1: ammonium acetate / 2-methoxy-ethanol; toluene / 90 - 95 °C 3.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 3.2: 16 h / 20 °C 3.3: 4 h / 60 °C 4.1: ammonium hydroxide / dichloromethane; water / 0.17 h 5.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
  • 21
  • C26H26BrN3O3 [ No CAS ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / tetrahydrofuran / 16 - 45 °C 2.1: ammonium acetate / 2-methoxy-ethanol; toluene / 90 - 95 °C 3.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 3.2: 4 h / 60 °C 4.1: ammonium hydroxide / dichloromethane; water / 0.17 h 5.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
  • 22
  • C44H55N5O10 [ No CAS ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: ammonium acetate / 2-methoxy-ethanol; toluene / 90 - 95 °C 2.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 2.2: 4 h / 60 °C 3.1: ammonium hydroxide / dichloromethane; water / 0.17 h 4.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
  • 23
  • C47H53N5O10 [ No CAS ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: ammonium acetate / 2-methoxy-ethanol; toluene / 90 - 95 °C 2.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 2.2: 16 h / 20 °C 2.3: 4 h / 60 °C 3.1: ammonium hydroxide / dichloromethane; water / 0.17 h 4.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
  • 24
  • C39H47N5O8 [ No CAS ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: ammonium acetate / 2-methoxy-ethanol; toluene / 90 - 95 °C 2.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 2.2: 4 h / 60 °C 3.1: ammonium hydroxide / dichloromethane; water / 0.17 h 4.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
  • 25
  • C47H53N7O7 [ No CAS ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 1.2: 16 h / 20 °C 1.3: 4 h / 60 °C 2.1: ammonium hydroxide / dichloromethane; water / 0.17 h 3.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
  • 26
  • tert-butyl (2S,4S)-2-[5-(2-{(2S,5S)-1-[N-(methoxycarbonyl)-L-valyl]-5-methylpyrrolidin-2-yl}-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-9-yl)-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidine-1-carboxylate [ No CAS ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 1.2: 4 h / 60 °C 2.1: ammonium hydroxide / dichloromethane; water / 0.17 h 3.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
  • 27
  • (2S,4S)-2-[5-(2-{(2S,4S)-1-{N-(methoxycarbonyl)-L-valyl}-5-methylpyrrolidin-2-yl}-1,11-dihydroisochromene[4',3':6,7]naphtho[1,2-d]imidazol-9-yl)-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidine [ No CAS ]
  • C11H11NO5 [ No CAS ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
89.9% With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In dichloromethane at 5 - 10℃; for 16h; 15 Example 15: Synthesis of Compound 1 50ml reaction flask,3.0 g of compound VLP-1 was added,1.34 g D-phenylglycine,1.0 ml N-methyl morpholineAnd 45 ml of dichloromethane,Stirring dissolved,Cooled to 5-10 ° C,A solution of 1.44 g of 4- (4,6-dimethoxytriazin-2-yl) -4-methylmorpholine hydrochloride (DMTMM)Reaction 16H,LC monitoring of the disappearance of raw material VLP-1,Add 10 ml of water to quench the reaction.Separate water,Followed by washing with 10% KHCO3, washed with water, dried over sodium sulfate,Concentration gave Compound VLP (3.44 g, purity 99.56%, yield 89.9%).
  • 28
  • C39H45N7O5*(x)H3O4P [ No CAS ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ammonium hydroxide / dichloromethane; water / 0.17 h 2: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
  • 29
  • C31H35NO8 [ No CAS ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: ammonium acetate / 2-methoxy-ethanol; toluene / 16 - 90 °C 2.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 3 h / 20 - 25 °C 2.2: 0.5 h 2.3: 0.17 h 3.1: potassium carbonate / tetrahydrofuran / 16 - 45 °C 4.1: ammonium acetate / 2-methoxy-ethanol; toluene / 90 - 95 °C 5.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 5.2: 4 h / 60 °C 6.1: ammonium hydroxide / dichloromethane; water / 0.17 h 7.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
Multi-step reaction with 7 steps 1.1: ammonium acetate / 2-methoxy-ethanol; toluene / 16 - 90 °C 2.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 3 h / 20 - 25 °C 3.1: potassium carbonate / tetrahydrofuran / 16 - 45 °C 4.1: ammonium acetate / 2-methoxy-ethanol; toluene / 90 - 95 °C 5.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 5.2: 4 h / 60 °C 6.1: ammonium hydroxide / dichloromethane; water / 0.17 h 7.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
  • 30
  • (2S,4S)-1-(benzyloxycarbonyl)-4-(methoxymethyl)-pyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: potassium carbonate / dichloromethane / 16 h / 30 - 35 °C 2.1: ammonium acetate / 2-methoxy-ethanol; toluene / 16 - 90 °C 3.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 3 h / 20 - 25 °C 4.1: potassium carbonate / tetrahydrofuran / 16 - 45 °C 5.1: ammonium acetate / 2-methoxy-ethanol; toluene / 90 - 95 °C 6.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 6.2: 16 h / 20 °C 6.3: 4 h / 60 °C 7.1: ammonium hydroxide / dichloromethane; water / 0.17 h 8.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / 16 h / 5 - 10 °C
  • 31
  • C26H27NO6 [ No CAS ]
  • [ 1377049-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / N,N-dimethyl-formamide / 20 - 25 °C / Industrial scale 2.1: ammonium acetate / toluene / 20 h / 80 - 100 °C / Inert atmosphere; Industrial scale 3.1: tribromopyridine / methanol; dichloromethane / 3 h / 10 - 15 °C / Industrial scale 4.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 - 40 °C / Inert atmosphere; Industrial scale 5.1: ammonium acetate / toluene / 20 h / 80 - 100 °C / Inert atmosphere; Industrial scale 6.1: manganese(IV) oxide / dichloromethane / 10 - 20 °C / Inert atmosphere; Industrial scale 6.2: 60 °C / Industrial scale 7.1: trifluorormethanesulfonic acid / methanol / 60 - 65 °C / Industrial scale 8.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile / 1 h / 10 - 15 °C / Industrial scale 8.2: 0 - 15 °C / Industrial scale
Historical Records

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4,4'-Bis(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)-1,1'-biphenyl tetrahydrochloride

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