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[ CAS No. 1001264-89-6 ] {[proInfo.proName]}

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Chemical Structure| 1001264-89-6
Chemical Structure| 1001264-89-6
Structure of 1001264-89-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1001264-89-6 ]

CAS No. :1001264-89-6 MDL No. :MFCD22124514
Formula : C24H32ClN5O2 Boiling Point : -
Linear Structure Formula :- InChI Key :GRZXWCHAXNAUHY-NSISKUIASA-N
M.W : 458.00 Pubchem ID :24788740
Synonyms :
GDC-0068;RG7440

Calculated chemistry of [ 1001264-89-6 ]

Physicochemical Properties

Num. heavy atoms : 32
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.54
Num. rotatable bonds : 7
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 133.42
TPSA : 81.59 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.67
Log Po/w (XLOGP3) : 2.46
Log Po/w (WLOGP) : 2.01
Log Po/w (MLOGP) : 2.04
Log Po/w (SILICOS-IT) : 3.1
Consensus Log Po/w : 2.66

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.04
Solubility : 0.0413 mg/ml ; 0.0000902 mol/l
Class : Moderately soluble
Log S (Ali) : -3.82
Solubility : 0.0697 mg/ml ; 0.000152 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.89
Solubility : 0.000587 mg/ml ; 0.00000128 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.55

Safety of [ 1001264-89-6 ]

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 [ 1001264-89-6 ]

* 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.

  • Downstream synthetic route of [ 1001264-89-6 ]

[ 1001264-89-6 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 1001270-64-9 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
90% With hydrogenchloride In 1,4-dioxane at 20℃; 14.19 Step 19:; The tert-butyl (S)-2-(4-chlorophenyl)-3-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-l-yl)-3-oxopropyl(isopropyl) carbamate (2.50 g, 4.48 mmol) was dissolved in dioxane (22.4 mL) and treated with 4M HCl in dioxane (22.4 mL, 89.6 mmol) at room temperature. The resulting solution was allowed to stir overnight to completion by LCMS analysis of the crude. The solution was concentrated in vacuo to afford a gel that was dissolved in a minimal amount of methanol (10 mL). The solution was transferred via pipette to stirred ether (300 mL) to afford a white precipitate of desired product. The addition was about half when the white precipitate melted into a yellow gel. The material was concentrated in vacuo to afford a yellow gel which was allowed to stand under reduced pressure overnight to yield (S)-2-(4-chlorophenyl)-l-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H- cyclopenta[d]pyrimidin-4-yl)piperazin-l-yl)-3-(isopropylamino)propan-l-one dihydrochloride as a light yellow powder (2.14 g, 90%). [00370] 1H NMR (D2O, 400 MHz) δ 8.39 (s, IH), 7.37-7.35 (d, J = 8.4 Hz, 2H), 7.23-7.20(d, J = 8.4 Hz, 2H), 5.29-5.25 (m, IH), 4.33-4.29 (m, IH), 4.14-4.10 (m, IH), 3.89-3.19 (m, HH), 2.23-2.17 (m, IH), 2.08-1.99 (m, IH), 1.20-1.18 (m, 6H), 0.98-0.96 (d, J = 6.8 Hz, 3H). MS (APCI+) [M+H] +458.
3.74 kg Stage #1: tert-butyl ((S)-2-(4-chlorophenyl)-3-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl)(isopropyl)carbamate With hydrogenchloride In water; toluene at 50℃; for 1h; Large scale; Stage #2: With sodium hydroxide In dichloromethane; water at 20℃; Large scale;
  • 2
  • [ 1491129-84-0 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: N-ethyl-N,N-diisopropylamine / methanol / 4 h / 50 °C / Inert atmosphere; Large scale 2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 15 h / 20 °C / Large scale 3.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 4.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 5.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 6.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 6.2: 20 h / 20 °C / Inert atmosphere; Large scale 6.3: 2 h / 20 °C / Inert atmosphere; Large scale 7.1: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C / Large scale 8.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 9.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 10.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 10.2: 20 °C / pH > 12 / Large scale
Multi-step reaction with 9 steps 1.1: N-ethyl-N,N-diisopropylamine / methanol / 4 h / 50 °C / Inert atmosphere; Large scale 2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 15 h / 20 °C / Large scale 3.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 4.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 5.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 6.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 6.2: 20 h / 20 °C / Inert atmosphere; Large scale 7.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 8.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 9.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 9.2: 20 °C / pH > 12 / Large scale
  • 3
  • [ 1491895-99-8 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 15 h / 20 °C / Large scale 2.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 3.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 5.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 5.2: 20 h / 20 °C / Inert atmosphere; Large scale 6.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 7.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 8.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 8.2: 20 °C / pH > 12 / Large scale
Multi-step reaction with 9 steps 1.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 15 h / 20 °C / Large scale 2.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 3.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 5.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 5.2: 20 h / 20 °C / Inert atmosphere; Large scale 5.3: 2 h / 20 °C / Inert atmosphere; Large scale 6.1: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C / Large scale 7.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 8.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 9.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 9.2: 20 °C / pH > 12 / Large scale
  • 4
  • [ 1491896-03-7 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 2.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 3.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 4.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 4.2: 20 h / 20 °C / Inert atmosphere; Large scale 5.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 6.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 7.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 7.2: 20 °C / pH > 12 / Large scale
Multi-step reaction with 8 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 2.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 3.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 4.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 4.2: 20 h / 20 °C / Inert atmosphere; Large scale 4.3: 2 h / 20 °C / Inert atmosphere; Large scale 5.1: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C / Large scale 6.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 7.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 8.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 8.2: 20 °C / pH > 12 / Large scale
  • 5
  • [ 1491896-05-9 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 2.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 3.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 3.2: 20 h / 20 °C / Inert atmosphere; Large scale 4.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 5.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 6.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 6.2: 20 °C / pH > 12 / Large scale
Multi-step reaction with 7 steps 1.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 2.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 3.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 3.2: 20 h / 20 °C / Inert atmosphere; Large scale 3.3: 2 h / 20 °C / Inert atmosphere; Large scale 4.1: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C / Large scale 5.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 6.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 7.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 7.2: 20 °C / pH > 12 / Large scale
  • 6
  • [ 1491896-08-2 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 2.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 2.2: 20 h / 20 °C / Inert atmosphere; Large scale 3.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 4.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 5.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 5.2: 20 °C / pH > 12 / Large scale
Multi-step reaction with 6 steps 1.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 2.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 2.2: 20 h / 20 °C / Inert atmosphere; Large scale 2.3: 2 h / 20 °C / Inert atmosphere; Large scale 3.1: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C / Large scale 4.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 5.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 6.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 6.2: 20 °C / pH > 12 / Large scale
  • 7
  • [ 1638220-58-2 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 1.2: 20 h / 20 °C / Inert atmosphere; Large scale 2.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 3.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 4.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 4.2: 20 °C / pH > 12 / Large scale
Multi-step reaction with 5 steps 1.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 1.2: 20 h / 20 °C / Inert atmosphere; Large scale 1.3: 2 h / 20 °C / Inert atmosphere; Large scale 2.1: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C / Large scale 3.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 4.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 5.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 5.2: 20 °C / pH > 12 / Large scale
  • 8
  • [ 63473-60-9 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -75 - -67 °C / Inert atmosphere; Large scale 1.2: 4 h / -66 °C / Inert atmosphere; Large scale 2.1: thionyl chloride / 3 h / -5 - 0 °C / Inert atmosphere; Large scale 3.1: sodium methylate / methanol / 2.5 h / 0 °C / Inert atmosphere; Large scale 3.2: 10 h / 0 - 25 °C / Inert atmosphere; Large scale 4.1: 2,6-dimethylpyridine; trichlorophosphate / toluene / 25 h / 50 - 70 °C / Inert atmosphere; Large scale 5.1: N-ethyl-N,N-diisopropylamine / methanol / 4 h / 50 °C / Inert atmosphere; Large scale 6.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 15 h / 20 °C / Large scale 7.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 8.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 9.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 10.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 10.2: 20 h / 20 °C / Inert atmosphere; Large scale 11.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 12.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 13.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 13.2: 20 °C / pH > 12 / Large scale
Multi-step reaction with 14 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -75 - -67 °C / Inert atmosphere; Large scale 1.2: 4 h / -66 °C / Inert atmosphere; Large scale 2.1: thionyl chloride / 3 h / -5 - 0 °C / Inert atmosphere; Large scale 3.1: sodium methylate / methanol / 2.5 h / 0 °C / Inert atmosphere; Large scale 3.2: 10 h / 0 - 25 °C / Inert atmosphere; Large scale 4.1: 2,6-dimethylpyridine; trichlorophosphate / toluene / 25 h / 50 - 70 °C / Inert atmosphere; Large scale 5.1: N-ethyl-N,N-diisopropylamine / methanol / 4 h / 50 °C / Inert atmosphere; Large scale 6.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 15 h / 20 °C / Large scale 7.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 8.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 9.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 10.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 10.2: 20 h / 20 °C / Inert atmosphere; Large scale 10.3: 2 h / 20 °C / Inert atmosphere; Large scale 11.1: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C / Large scale 12.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 13.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 14.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 14.2: 20 °C / pH > 12 / Large scale
  • 9
  • [ 1001180-45-5 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 3.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 3.2: 20 °C / pH > 12 / Large scale
Multi-step reaction with 3 steps 1.1: hydrogenchloride / 1,4-dioxane / 20 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C 2.2: 1 h / 20 °C 3.1: hydrogenchloride / 1,4-dioxane / 20 °C
  • 10
  • [ 1638220-59-3 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C / Large scale 2.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 3.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 4.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 4.2: 20 °C / pH > 12 / Large scale
  • 11
  • [ 1878-66-6 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: pivaloyl chloride; triethylamine / toluene / Reflux; Inert atmosphere; Large scale 2.1: titanium tetrachloride / toluene; dichloromethane / 2 h / -20 - 10 °C / Inert atmosphere; Large scale 2.2: 3.5 h / -20 - -10 °C / Inert atmosphere; Large scale 2.3: 5 h / -20 - -10 °C / Inert atmosphere; Large scale 3.1: lithium hydroxide monohydrate; dihydrogen peroxide / tetrahydrofuran; water / 3 h / 0 °C / Large scale 4.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 5.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 5.2: 20 °C / pH > 12 / Large scale
Multi-step reaction with 11 steps 1.1: sulfuric acid / 20 °C 2.1: sodium methylate / dimethyl sulfoxide / 2 h / 20 °C 3.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0.5 h / 0 °C 4.1: tetrahydrofuran / 0 - 20 °C 5.1: tetrahydrofuran 6.1: tetrahydrofuran / 20 °C 7.1: tetrahydrofuran / 3 h / 20 °C 8.1: n-butyllithium / tetrahydrofuran; hexanes / 1 h / -78 °C 8.2: -78 - 20 °C 9.1: lithium hydroxide; water; dihydrogen peroxide / tetrahydrofuran / 0 - 20 °C 9.2: pH 2 - 3 10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C 10.2: 1 h / 20 °C 11.1: hydrogenchloride / 1,4-dioxane / 20 °C
  • 12
  • [ 220041-96-3 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: titanium tetrachloride / toluene; dichloromethane / 2 h / -20 - 10 °C / Inert atmosphere; Large scale 1.2: 3.5 h / -20 - -10 °C / Inert atmosphere; Large scale 1.3: 5 h / -20 - -10 °C / Inert atmosphere; Large scale 2.1: lithium hydroxide monohydrate; dihydrogen peroxide / tetrahydrofuran; water / 3 h / 0 °C / Large scale 3.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 4.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 4.2: 20 °C / pH > 12 / Large scale
  • 13
  • [ 1396256-89-5 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hydroxide monohydrate; dihydrogen peroxide / tetrahydrofuran; water / 3 h / 0 °C / Large scale 2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 3.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 3.2: 20 °C / pH > 12 / Large scale
  • 14
  • [ CAS Unavailable ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetramethyl ammoniumhydroxide / water; acetonitrile / 20 °C / Large scale 1.2: 5 h / 15 - 25 °C / Large scale 2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 3.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 3.2: 20 °C / pH > 12 / Large scale
  • 15
  • [ 1001179-33-4 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 2.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 2.2: 20 °C / pH > 12 / Large scale
  • 16
  • [ 1001269-85-7 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 2.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 2.2: 20 °C / pH > 12 / Large scale
  • 18
  • [ 126672-25-1 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1.1: thionyl chloride / 3 h / -5 - 0 °C / Inert atmosphere; Large scale 2.1: sodium methylate / methanol / 2.5 h / 0 °C / Inert atmosphere; Large scale 2.2: 10 h / 0 - 25 °C / Inert atmosphere; Large scale 3.1: 2,6-dimethylpyridine; trichlorophosphate / toluene / 25 h / 50 - 70 °C / Inert atmosphere; Large scale 4.1: N-ethyl-N,N-diisopropylamine / methanol / 4 h / 50 °C / Inert atmosphere; Large scale 5.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 15 h / 20 °C / Large scale 6.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 7.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 8.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 9.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 9.2: 20 h / 20 °C / Inert atmosphere; Large scale 10.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 11.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 12.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 12.2: 20 °C / pH > 12 / Large scale
Multi-step reaction with 13 steps 1.1: thionyl chloride / 3 h / -5 - 0 °C / Inert atmosphere; Large scale 2.1: sodium methylate / methanol / 2.5 h / 0 °C / Inert atmosphere; Large scale 2.2: 10 h / 0 - 25 °C / Inert atmosphere; Large scale 3.1: 2,6-dimethylpyridine; trichlorophosphate / toluene / 25 h / 50 - 70 °C / Inert atmosphere; Large scale 4.1: N-ethyl-N,N-diisopropylamine / methanol / 4 h / 50 °C / Inert atmosphere; Large scale 5.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 15 h / 20 °C / Large scale 6.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 7.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 8.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 9.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 9.2: 20 h / 20 °C / Inert atmosphere; Large scale 9.3: 2 h / 20 °C / Inert atmosphere; Large scale 10.1: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C / Large scale 11.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 12.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 13.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 13.2: 20 °C / pH > 12 / Large scale
  • 19
  • [ 1076218-98-8 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: sodium methylate / methanol / 2.5 h / 0 °C / Inert atmosphere; Large scale 1.2: 10 h / 0 - 25 °C / Inert atmosphere; Large scale 2.1: 2,6-dimethylpyridine; trichlorophosphate / toluene / 25 h / 50 - 70 °C / Inert atmosphere; Large scale 3.1: N-ethyl-N,N-diisopropylamine / methanol / 4 h / 50 °C / Inert atmosphere; Large scale 4.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 15 h / 20 °C / Large scale 5.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 6.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 7.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 8.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 8.2: 20 h / 20 °C / Inert atmosphere; Large scale 9.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 10.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 11.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 11.2: 20 °C / pH > 12 / Large scale
Multi-step reaction with 12 steps 1.1: sodium methylate / methanol / 2.5 h / 0 °C / Inert atmosphere; Large scale 1.2: 10 h / 0 - 25 °C / Inert atmosphere; Large scale 2.1: 2,6-dimethylpyridine; trichlorophosphate / toluene / 25 h / 50 - 70 °C / Inert atmosphere; Large scale 3.1: N-ethyl-N,N-diisopropylamine / methanol / 4 h / 50 °C / Inert atmosphere; Large scale 4.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 15 h / 20 °C / Large scale 5.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 6.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 7.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 8.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 8.2: 20 h / 20 °C / Inert atmosphere; Large scale 8.3: 2 h / 20 °C / Inert atmosphere; Large scale 9.1: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C / Large scale 10.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 11.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 12.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 12.2: 20 °C / pH > 12 / Large scale
  • 20
  • [ 1245646-90-5 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: 2,6-dimethylpyridine; trichlorophosphate / toluene / 25 h / 50 - 70 °C / Inert atmosphere; Large scale 2.1: N-ethyl-N,N-diisopropylamine / methanol / 4 h / 50 °C / Inert atmosphere; Large scale 3.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 15 h / 20 °C / Large scale 4.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 5.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 6.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 7.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 7.2: 20 h / 20 °C / Inert atmosphere; Large scale 8.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 9.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 10.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 10.2: 20 °C / pH > 12 / Large scale
Multi-step reaction with 11 steps 1.1: 2,6-dimethylpyridine; trichlorophosphate / toluene / 25 h / 50 - 70 °C / Inert atmosphere; Large scale 2.1: N-ethyl-N,N-diisopropylamine / methanol / 4 h / 50 °C / Inert atmosphere; Large scale 3.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 15 h / 20 °C / Large scale 4.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 5.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 6.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 7.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 7.2: 20 h / 20 °C / Inert atmosphere; Large scale 7.3: 2 h / 20 °C / Inert atmosphere; Large scale 8.1: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C / Large scale 9.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 10.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 11.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 11.2: 20 °C / pH > 12 / Large scale
  • 21
  • [ 65844-74-8 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1.1: Chromobacterium strain SC-YM-1 / aq. phosphate buffer / 19 h / 0 °C / pH 7 - 7.6 / Resolution of racemate; Microbiological reaction; Large scale 2.1: sodium methylate / methanol / 2.5 h / 0 °C / Inert atmosphere; Large scale 2.2: 10 h / 0 - 25 °C / Inert atmosphere; Large scale 3.1: 2,6-dimethylpyridine; trichlorophosphate / toluene / 25 h / 50 - 70 °C / Inert atmosphere; Large scale 4.1: N-ethyl-N,N-diisopropylamine / methanol / 4 h / 50 °C / Inert atmosphere; Large scale 5.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 15 h / 20 °C / Large scale 6.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 7.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 8.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 9.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 9.2: 20 h / 20 °C / Inert atmosphere; Large scale 10.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 11.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 12.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 12.2: 20 °C / pH > 12 / Large scale
Multi-step reaction with 13 steps 1.1: Chromobacterium strain SC-YM-1 / aq. phosphate buffer / 19 h / 0 °C / pH 7 - 7.6 / Resolution of racemate; Microbiological reaction; Large scale 2.1: sodium methylate / methanol / 2.5 h / 0 °C / Inert atmosphere; Large scale 2.2: 10 h / 0 - 25 °C / Inert atmosphere; Large scale 3.1: 2,6-dimethylpyridine; trichlorophosphate / toluene / 25 h / 50 - 70 °C / Inert atmosphere; Large scale 4.1: N-ethyl-N,N-diisopropylamine / methanol / 4 h / 50 °C / Inert atmosphere; Large scale 5.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 15 h / 20 °C / Large scale 6.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 7.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 8.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 9.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 9.2: 20 h / 20 °C / Inert atmosphere; Large scale 9.3: 2 h / 20 °C / Inert atmosphere; Large scale 10.1: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C / Large scale 11.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 12.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 13.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 13.2: 20 °C / pH > 12 / Large scale
  • 22
  • [ 1001264-89-6 ]
  • [ 98-11-3 ]
  • [ 1491138-23-8 ]
YieldReaction ConditionsOperation in experiment
In butanone 5 Example 5 (S)-2-(4-chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yppiperazin-1-yl)-3-(isopropylamino)propan-1-one Benzene Sulfonic Acid Salt S)-2-(4-Chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yppiperazin-1-yl)-3-(isopropylamino)propan-1-one free base (113.99 mg) was dissolved in methyl ethyl ketone (1 mL) Benzenesulfonic acid (39.98 mg) was dissolved in methyl ethyl ketone and the acid solution added to the solution of free base. Solid formed. Additional methyl ethyl ketone was added to ensure that the suspension could be mixed. The suspension was stirred overnight and the benzenesulfonic acid salt was isolated by filtration and dried in a vacuum oven for 2 hours at 50° C. The benzenesulfonic acid salt from above, 10.2 mg, was placed into a 20 mL vial, acetonitrile, 0.2 mL, added and the vial placed into a shaking block at 22° C. The slurry was shaken for 8 days to give a mixture of needles and plates. Single crystal structure determination was conducted on one of the plates from the slurry (See ), and the data is shown in Table 2 below.
  • 23
  • [ 1001264-89-6 ]
  • [ 104-15-4 ]
  • [ 1491138-24-9 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile 6 Example 6 (S)-2-(4-chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-(isopropylamino)propan-1-one p-toluene Sulfonic Acid Salt S)-2-(4-Chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-(isopropylamino)propan-1-one free base, 202.4 mg, was dissolved in acetonitrile, 10 mL. p-Toluenesulfonic acid monohydrate, 83.5 mg, was dissolved in acetonitrile, 10 mg, and the two solutions mixed. The solution was slowly evaporated under a stream of nitrogen. The crystaline tosylate salt was analyzed after evaporating over 3 weeks (See ).
  • 24
  • [ 109135-06-0 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0.5 h / 0 °C 2.1: tetrahydrofuran / 0 - 20 °C 3.1: tetrahydrofuran 4.1: tetrahydrofuran / 20 °C 5.1: tetrahydrofuran / 3 h / 20 °C 6.1: n-butyllithium / tetrahydrofuran; hexanes / 1 h / -78 °C 6.2: -78 - 20 °C 7.1: lithium hydroxide; water; dihydrogen peroxide / tetrahydrofuran / 0 - 20 °C 7.2: pH 2 - 3 8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C 8.2: 1 h / 20 °C 9.1: hydrogenchloride / 1,4-dioxane / 20 °C
  • 25
  • [ 1000985-03-4 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: tetrahydrofuran 2.1: tetrahydrofuran / 20 °C 3.1: tetrahydrofuran / 3 h / 20 °C 4.1: n-butyllithium / tetrahydrofuran; hexanes / 1 h / -78 °C 4.2: -78 - 20 °C 5.1: lithium hydroxide; water; dihydrogen peroxide / tetrahydrofuran / 0 - 20 °C 5.2: pH 2 - 3 6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C 6.2: 1 h / 20 °C 7.1: hydrogenchloride / 1,4-dioxane / 20 °C
  • 26
  • [ 1000985-04-5 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: tetrahydrofuran / 20 °C 2.1: tetrahydrofuran / 3 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexanes / 1 h / -78 °C 3.2: -78 - 20 °C 4.1: lithium hydroxide; water; dihydrogen peroxide / tetrahydrofuran / 0 - 20 °C 4.2: pH 2 - 3 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C 5.2: 1 h / 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 20 °C
  • 27
  • [ 1001178-87-5 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: trichlorophosphate / 0.08 h / Heating / reflux 2.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 48 h / 20 °C 2.2: 0.33 h / 0 °C 3.1: 2 h / 110 °C 4.1: 1-methyl-pyrrolidin-2-one / 12 h / 110 °C 5.1: lithium hydroxide; water / tetrahydrofuran / 6 h / 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 20 h / 20 °C 7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C 7.2: 1 h / 20 °C 8.1: hydrogenchloride / 1,4-dioxane / 20 °C
  • 28
  • [ 953045-35-7 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 48 h / 20 °C 1.2: 0.33 h / 0 °C 2.1: 2 h / 110 °C 3.1: 1-methyl-pyrrolidin-2-one / 12 h / 110 °C 4.1: lithium hydroxide; water / tetrahydrofuran / 6 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 20 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C 6.2: 1 h / 20 °C 7.1: hydrogenchloride / 1,4-dioxane / 20 °C
  • 29
  • [ 1001180-35-3 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: 17 h / 150 °C 2.1: trichlorophosphate / 0.08 h / Heating / reflux 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 48 h / 20 °C 3.2: 0.33 h / 0 °C 4.1: 2 h / 110 °C 5.1: 1-methyl-pyrrolidin-2-one / 12 h / 110 °C 6.1: lithium hydroxide; water / tetrahydrofuran / 6 h / 20 °C 7.1: hydrogenchloride / 1,4-dioxane / 20 h / 20 °C 8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C 8.2: 1 h / 20 °C 9.1: hydrogenchloride / 1,4-dioxane / 20 °C
  • 30
  • [ 1001178-85-3 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: ammonia; water / nickel / 3 h / Heating / reflux 2.1: trichlorophosphate / 0.08 h / Heating / reflux 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 48 h / 20 °C 3.2: 0.33 h / 0 °C 4.1: 2 h / 110 °C 5.1: 1-methyl-pyrrolidin-2-one / 12 h / 110 °C 6.1: lithium hydroxide; water / tetrahydrofuran / 6 h / 20 °C 7.1: hydrogenchloride / 1,4-dioxane / 20 h / 20 °C 8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C 8.2: 1 h / 20 °C 9.1: hydrogenchloride / 1,4-dioxane / 20 °C
  • 31
  • [ 1402155-45-6 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexanes / 1 h / -78 °C 1.2: -78 - 20 °C 2.1: lithium hydroxide; water; dihydrogen peroxide / tetrahydrofuran / 0 - 20 °C 2.2: pH 2 - 3 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C 3.2: 1 h / 20 °C 4.1: hydrogenchloride / 1,4-dioxane / 20 °C
  • 32
  • [ 1001180-18-2 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.58 h / -78 °C 1.2: 0.5 h / -78 - 20 °C 2.1: formic acid; triethylamine / Ru catalyst / dichloromethane / 18 h 3.1: hydrogenchloride / 1,4-dioxane / 20 h / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C 4.2: 1 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 20 °C
Multi-step reaction with 5 steps 1.1: triethylamine / dichloromethane / 20 °C 2.1: lithium hydroxide; water / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: hydrogenchloride / 1,4-dioxane / 20 h / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C 4.2: 1 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 20 °C
  • 33
  • [ 1001180-21-7 ]
  • (2S)-2-(4-chlorophenyl)-1-[4-[(5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-yiamino)propan-1-one [ No CAS ]
  • 34
  • [ 1001180-15-9 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: ethanol; hexane 2.1: lithium hydroxide; water / tetrahydrofuran / 6 h / 20 °C 3.1: hydrogenchloride / 1,4-dioxane / 20 h / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C 4.2: 1 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 20 °C
Multi-step reaction with 6 steps 1.1: lithium hydroxide; water / tetrahydrofuran / 4.66 h / 0 - 20 °C 1.2: 0.08 h / 0 °C 2.1: triethylamine / dichloromethane / 20 °C 3.1: lithium hydroxide; water / tetrahydrofuran / 1 h / 0 - 20 °C 4.1: hydrogenchloride / 1,4-dioxane / 20 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C 5.2: 1 h / 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 20 °C
Multi-step reaction with 6 steps 1.1: lithium hydroxide; water / tetrahydrofuran / 4.66 h / 0 - 20 °C 1.2: 0.08 h / 0 °C 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.58 h / -78 °C 2.2: 0.5 h / -78 - 20 °C 3.1: formic acid; triethylamine / Ru catalyst / dichloromethane / 18 h 4.1: hydrogenchloride / 1,4-dioxane / 20 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C 5.2: 1 h / 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 20 °C
  • 35
  • [ 1001179-31-2 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hydroxide; water; dihydrogen peroxide / tetrahydrofuran / 0 - 20 °C 1.2: pH 2 - 3 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C 2.2: 1 h / 20 °C 3.1: hydrogenchloride / 1,4-dioxane / 20 °C
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