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[ CAS No. 1403898-64-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1403898-64-5
Chemical Structure| 1403898-64-5
Chemical Structure| 1403898-64-5
Structure of 1403898-64-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1403898-64-5 ]

CAS No. :1403898-64-5 MDL No. :MFCD28100885
Formula : C11H22N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :OCHKRKFPKUAHGF-RKDXNWHRSA-N
M.W : 230.30 Pubchem ID :71003242
Synonyms :

Calculated chemistry of [ 1403898-64-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.91
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 69.28
TPSA : 61.8 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.62
Log Po/w (XLOGP3) : 0.27
Log Po/w (WLOGP) : -0.19
Log Po/w (MLOGP) : 0.32
Log Po/w (SILICOS-IT) : 0.1
Consensus Log Po/w : 0.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.17
Solubility : 15.4 mg/ml ; 0.067 mol/l
Class : Very soluble
Log S (Ali) : -1.13
Solubility : 17.1 mg/ml ; 0.0743 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.04
Solubility : 21.0 mg/ml ; 0.091 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.28

Safety of [ 1403898-64-5 ]

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 [ 1403898-64-5 ]

* 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 [ 1403898-64-5 ]

[ 1403898-64-5 ] Synthesis Path-Downstream   1~96

  • 1
  • [ 1403898-64-5 ]
  • [ 501-53-1 ]
  • [ 1403898-70-3 ]
YieldReaction ConditionsOperation in experiment
87% With sodium hydroxide; In tetrahydrofuran; water; at 0 - 10℃; for 1h;Inert atmosphere; A solution of 180 <strong>[1403898-64-5]tert-butyl (2R,5R)-5-(hydroxymethyl)-2-methylpiperazine-1-carboxylate</strong> (18.5 g, 80.33 mmol) in 78 THF (190 ml) was cooled in an ice-bath to 0 C. Aqueous 1M 38 sodium hydroxide solution (88 ml, 88.36 mmol) was added, followed by 317 benzyl chloroformate (11.99 ml, 84.34 mmol) (internal reaction temperature kept 57 ethyl acetate in 58 heptane. Pure fractions were evaporated to dryness to afford 318 1-benzyl 4-tert-butyl (2R,5R)-2-(hydroxymethyl)-5-methylpiperazine-1,4-dicarboxylate (25.4 g, 87%) as a colourless oil. 1H NMR (400 MHz, CD3OD, 30 C.): 1.12 (3H, dd), 1.46 (9H, s), 3.1-3.29 (2H, m), 3.53-3.66 (2H, m), 3.81 (1H, d), 3.88-4.02 (1H, m), 4.15-4.38 (2H, m), 5.06-5.26 (2H, m), 7.21-7.51 (5H, m). One exchangeable proton not seen. m/z: ES+ [M-Boc]=265.1.
With sodium hydroxide; In tetrahydrofuran; at 3 - 4℃; for 2h; Preparation 10: (2R,5R)-2-Hydroxymethyl-5-methyl-piperazine-1 ,4-dicarboxylic acid 1 - benzyl ester 4-ferf-butyl esterTo (2R,5R)-5-hydroxymethyl-2-methyl-piperazine-1 -carboxylic acid ie f-butyl ester (21 g, 90 mmol) in THF (210 mL) at 3-4 C (ice bath) was added 1 M aqueous NaOH (99.5 mL) and benzyl chloroformate (12.9 mL, 90.43 mmol). After stirring for 1 h at the same temperature, the mixture was left to stir for another 1 h and then warmed to RT. The organic layer was separated and the aqueous phase extracted with EtOAc (2 x 50 mL). The combined organic extracts were washed with saturated brine solution (150 mL), then dried over sodium sulfate, filtered and concentrated. The crude oil was purified by column chromatography on silica gel (gradient elution, 0 - 100%, EtOAc/petrol), to give the title compound (26 g) as a pale yellow oil, used directly in Preparation 1 1 . 1H NMR (Me-d3-OD): 7.47-7.15 (5H, m), 5.26-5.07 (2H, m), 4.25 (2H, s), 4.04-3.88 (1 H, m), 3.83 (1 H, d), 3.61 (2H, bs), 3.31 -3.09 (2H, m), 1 .48 (9H, s), 1.14 (3H, t).
  • 2
  • [ 67-56-1 ]
  • tert-butyl dicarbonate [ No CAS ]
  • [ 142-64-3 ]
  • [ 1403898-64-5 ]
YieldReaction ConditionsOperation in experiment
75% Preparation 5: (2R,5R)-5-Hydroxymethyl-2-methyl-piperazine-1 -carboxylic acid ferf-butyl ester. To the piperazine dihydrochloride (20 g, 1 19 mmol) in MeOH (96 mL) at 0 C (ice bath) was added triethylamine (48.7 mL, 357 mmol). ie f-Butyl dicarbonate (61 g, 280 mmol) in MeOH (145 mL) was added over 30 min. The reaction temperature was maintained at <10 C for 1 h, warmed to ambient temperature over 1 h and then heated to 50 C for 18 h. The reaction was concentrated and the residue dissolved in ethanol (397 mL). A solution of NaOH (23.8 g, 595 mmol) in water (397 mL) was added and the reaction heated to 100 C for 18 h, then cooled to ambient temperature. Mixture was neutralised with 1 M HCI (-300 mL) to pH 9 (using a pH meter), then extracted with chloroform (3 x 700 mL), dried over sodium sulfate, filtered and concentrated. The residue was redissolved in MeOH and concentrated, then dried in vacuo at 40 C, to give the title compound (21 g, 75%) as a colourless solid. 1H NMR (Me-d3- OD): 4.20-4.07 (1 H, m), 3.79 (1 H, dd), 3.71 -3.58 (2H, m), 3.54 (1 H, dd), 3.24 (1 H, dd), 3.18- 3.01 (1 H, m), 3.01 -2.89 (1 H, m), 2.55 (1 H, dd), 1.48 (9H, s), 1.25 (3H, s).
  • 4
  • [ 1403898-64-5 ]
  • [ 1403898-67-8 ]
  • 5
  • [ 1403898-64-5 ]
  • [ 1403898-69-0 ]
  • 6
  • [ 1403898-64-5 ]
  • (2R,5R)-5-methyl-piperazine-1,2,4-tricarboxylic acid 1-benzyl ester 4-tert-butyl ester [ No CAS ]
  • 7
  • [ 1403898-60-1 ]
  • [ 1403898-64-5 ]
  • [ 1403898-65-6 ]
YieldReaction ConditionsOperation in experiment
75% With tetrahydrofuran; triethylamine; at 65℃; for 3h; Preparation 6: (2R,5R)-4-[2-(6-Chloro-3,3-dimethyl-2,3-dihydro-indol-1 -yl)-2-oxo-ethyl]-5- hydroxymethyl-2-methyl-piperazine-1 -carboxylic acid ferf-butyl esterTo 2-chloro-1 -(6-chloro-3,3-dimethyl-2,3-dihydro-indol-1 -yl)-ethanone (397 mg, 1 .31 mmol) in anhydrous THF (1 .23 mL) was added triethylamine (366 mu, 2.60 mmol) and a solution of (2R,5R)-5-hydroxymethyl-2-methyl-piperazine-1 -carboxylic acid ferf-butyl ester (380 mg, 1 .6 mmol) in anhydrous THF (730 mu). The reaction was heated to 65 C for 3 h, cooled to ambient temperature and the solvent removed in vacuo. The residue was purified by columnchromatography on silica gel (gradient elution, 0-80%, EtOAc/petrol), to give the title compound (447 mg, 75%) as a colourless solid. 1H NMR (Me-d3-OD): 8.15 (1 H, d), 7.20 (1 H, d), 7.09 (1 H, dd), 5.51 (2H, s), 4.23-4.13 (1 H, m), 4.09-3.96 (3H, m), 3.81 -3.65 (2H, m), 3.64-3.47 (2H, m), 2.97-2.82 (2H, m), 2.67 (1 H, dd), 1.48 (9H, s), 1.37 (6H, s), 1 .26-1 .22 (3H, m).
  • 8
  • [ 1403898-62-3 ]
  • [ 1403898-64-5 ]
  • 9
  • [ 24424-99-5 ]
  • ((2R,5R)-5-methyl-piperazin-2-yl)-methanol hydrochloride [ No CAS ]
  • [ 1403898-64-5 ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine; In methanol; at 0 - 50℃; for 20.5h; To ((2R,5R)-5-methyl-piperazin-2-yl)-methanol hydrochloride (20 g, 119 mmol) in MeOH (96 mL) at 0 C (ice bath) was added triethylamine (48.7 mL, 357 mmol). teit-Butyl dicarbonate (61 g, 280 mmol) in MeOH (145 mL) was added over 30 mm. The reaction temperature was maintained at <10 c for 1 h, warmed to ambient temperature over 1 h and then heated to 50 00 for 18 h. The reaction was concentrated and the residue dissolved in ethanol (397 mL). Asolution of NaOH (23.8 g, 595 mmol) in water (397 mL) was added and the reaction heated to 100 00 for 18 h, then cooled to ambient temperature. Mixture was neutralised with 1M HCI (-300 mL) to pH 9 (using a pH meter), then extracted with chloroform (3 x 700 mL), dried over sodium sulfate, filtered and concentrated. The residue was redissolved in MeOH and concentrated, then dried in vacuo at 40 c to give the title compound (21 g, 75%) as acolourless solid. 1H NMR (Me-d3-OD): 4.20-4.07 (1H, m), 3.79 (1H, dd), 3.71-3.58 (2H, m),3.54 (1H, dd), 3.24 (1H, dd), 3.18-3.01 (1H, m), 3.01-2.89 (1H, m), 2.55 (1H, dd), 1.48 (9H,5), 1.25 (3H, 5).
75% Preparation 4: (2R,5R)-5-Hydroxymethyl-2-methyl-pi perazi ne-I -carboxylic acid tert-butyl esterTo ((2R,5R)-5-methyl-piperazin-2-yl)-methanol hydrochloride (20 g, 119 mmol) in MeOH (96mL) at 0 C (ice bath) was added triethylamine (48.7 mL, 357 mmol). teit-Butyl dicarbonate (61g, 280 mmol) in MeOH (145 mL) was added over 30 mm. The reaction temperature wasmaintained at <10 c for 1 h, warmed to ambient temperature over 1 h and then heated to 50 cfor 18 h. The reaction was concentrated and the residue dissolved in ethanol (397 mL). Asolution of NaOH (23.8 g, 595 mmol) in water (397 mL) was added and the reaction heated to100 00 for 18 h, then cooled to ambient temperature. Mixture was neutralised with 1M HCI(-300 mL) to pH 9 (using a pH meter), then extracted with chloroform (3 x 700 mL), dried over sodium sulfate, filtered and concentrated. The residue was redissolved in MeOH andconcentrated, then dried in vacuo at 40 c to give the title compound (21 g, 75%) as acolourless solid. 1H NMR (Me-d3-OD): 4.20-4.07 (1H, m), 3.79 (1H, dd), 3.71-3.58 (2H, m), 3.54 (1H, dd), 3.24 (1H, dd), 3.18-3.01 (1H, m), 3.01-2.89 (1H, m), 2.55 (1H, dd), 1.48 (9H, 5), 1.25 (3H, 5).
75% To ((2 R, 5R)-5-methyl-pi perazin-2-yl)-methanol hydrochloride (which may be prepared asdescribed in Preparation 3) (20 g, 119 mmol) in MeOH (96 mL) at 0C (ice bath) was added triethylamine (48.7 mL, 357 mmol). teit-Butyl dicarbonate (61 g, 280 mmol) in MeOH (145 mL) was added over 30 mm. The reaction temperature was maintained at <10 c for 1 h, warmed to ambient temperature over 1 h and then heated to 50 c for 18 h. The reaction was concentrated and the residue dissolved in ethanol (397 mL). A solution of NaOH (23.8 g, 595 mmol) in water(397 mL) was added and the reaction heated to 100 c for 18 h, then cooled to ambient temperature. Mixture was neutralised with 1 M HCI (-300 mL) to pH 9 (using a pH meter), then extracted with chloroform (3 x 700 mL), dried over sodium sulfate, filtered and concentrated. The residue was redissolved in MeOH and concentrated, then dried in vacuo at 40 C to give the title compound (21 g, 75%) as a colourless solid. 1H NMR (Me-d3-OD): 4.20-4.07 (1H, m),3.79 (1H, dd), 3.71-3.58 (2H, m), 3.54 (1H, dd), 3.24 (1H, dd), 3.18-3.01 (1H, m), 3.01-2.89 (1H, m), 2.55 (1H, dd), 1.48 (9H, 5), 1.25 (3H, 5).
  • 10
  • [ 1403898-64-5 ]
  • 1-[(2R,5R)-1-(2-{6-[(4-fluorophenyl)methyl]-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl}2-oxo-ethyl)-5-methylpiperazin-2-yl]methyl}-1H-imidazole-2-carbonitrile L-lactate [ No CAS ]
  • 13
  • [ 1403898-64-5 ]
  • [ 1604817-73-3 ]
  • 14
  • [ 1403898-64-5 ]
  • [ 100-52-7 ]
  • [ 1403901-32-5 ]
YieldReaction ConditionsOperation in experiment
74% With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 18h; A mixture of (2 R,5R)-5-hydroxymethyl-2-methyl-piperazine- 1 -carboxylic acid tert-butyl ester (3.48 g, 15.1 mmol), benzaldehyde (1.76 g, 16.6 mmol), sodium triacetoxyborohydride (3.84 g, 18.1 mmol) and 1 ,2-dichloroethane (30 mL) was stirred at 20 c for 18 h, then partitionedbetween saturated aqueous NaHCO3 (150 mL) and DCM (3 x 50 mL). Combined organic extracts were dried (Na2SO4) then evaporated in vacuo to give an oil. Chromatography (Si02, 0 - 30% EtOAc in petrol) gave the title compound (4.588 g, 74%) as a colourless solid. MS: [M+H] = 321.
74% With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 18h; Preparation 5: (2R,5R)-4-Benzyl-5-hydroxymethyl-2-methyl-pi perazi ne-I -carboxylic acidtert-butyl ester A mixture of (2 R,5R)-5-hydroxymethyl-2-methyl-piperazine- 1 -carboxylic acid tert-butyl ester(3.48 g, 15.1 mmol), benzaldehyde (1.76 g, 16.6 mmol), sodium triacetoxyborohydride (3.84 g,18.1 mmol) and 1,2-dichloroethane (30 mL)was stirred at2O c for 18 h, then partitionedbetween saturated aqueous NaHCO3 (150 mL) and DCM (3 x 50 mL). Combined organic extracts were dried (Na2SO4) then evaporated in vacuo to give an oil. Chromatography (Si02, 0- 30% EtOAc in petrol) gave the title compound (4.588 g, 74%) as a colourless solid. MS:[M+H] = 321.
74% With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 18h; Preparation 5: (2R,5R)-4-Benzyl-5-hydroxymethyl-2-methyl-pi perazi ne-I -carboxyl icacid tert-butyl esterA mixture of (2 R,5R)-5-hydroxymethyl-2-methyl-piperazine- 1 -carboxylic acid tert-butyl ester (3.48 g, 15.1 mmol), benzaldehyde (1.76 g, 16.6 mmol), sodium triacetoxyborohydride (3.84 g, 18.1 mmol) and 1 ,2-dichloroethane (30 mL) was stirred at 20 c for 18 h, then partitionedbetween saturated aqueous NaHCO3 (150 mL) and DCM (3 x 50 mL). Combined organic extracts were dried (Na2SO4) then evaporated in vacuo to give an oil. Chromatography (Si02, 0 - 30% EtOAc in petrol) gave the title compound (4.588 g, 74%) as a colourless solid. MS: [M+H] = 321.
74% With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 18h; A mixture of (2R ,5R)-5-hydroxymethyl-2-methyl-piperazine- 1 -carboxylic acid tert-butyl ester(which may be prepared as described in Preparation 4) (3.48 g, 15.1 mmol), benzaldehyde(1.76 g, 16.6 mmol), sodium triacetoxyborohydride (3.84 g, 18.1 mmol) and 1,2-dichloroethane(30 mL) was stirred at 20 C for 18 h, then partitioned between saturated aqueous NaHCO3(150 mL) and DCM (3 x 50 mL). Combined organic extracts were dried (Na2SO4) thenevaporated in vacuo to give an oil. Chromatography (Si02, 0 - 30% EtOAc in petrol) gave the title compound (4.588 g, 74%) as a colourless solid. MS: [M+H] = 321.

  • 15
  • [ 1403898-64-5 ]
  • 2-chloro-1-[6-(4-fluorobenzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-ethanone hydrochloride [ No CAS ]
  • [ 1403903-27-4 ]
YieldReaction ConditionsOperation in experiment
12.14 g With potassium carbonate; potassium iodide; In acetonitrile; at 20℃;Inert atmosphere; Finely ground potassium iodide (7.5 g, 45.26 mmol) was added to a mixture of (2R,5R)-5- hydroxymethyl-2-methyl-piperazine- 1 -carboxylic acid teit-butyl ester (5.7 g, 24.89 mmol), 2- chloro- 1 -[6-(4-fluorobenzyl)-3, 3-dimethyl-2, 3-dihydro-pyrrolo[3,2-b]pyridin- 1 -yl]-ethanone hydrochloride (8.35 g, 22.63 mmol) potassium carbonate (12.5 g, 90.51 mmol) andacetonitrile (100 mL) under nitrogen. The mixture was stirred at 20 C overnight. The mixture was partitioned between water (300 mL) and EtOAc (300 mL) and the organic phase was dried and evaporated in vacuo to give the title compound (12.14 g). MS: [M+H] = 527.
12.14 g With potassium carbonate; potassium iodide; In acetonitrile; at 20℃;Inert atmosphere; Preparation 22: (2R,5R)-4-{2-[6-(4-FI uoro-benzyl)-3,3-di methyl-2,3-di hydro-pyrrolo[3,2- b]pyridi n-I -yI]-2-oxo-ethyl}-5-hydroxymethyl-2-methyl-pi perazi ne-I -carboxylic acid tertbutyl esterFinely ground potassium iodide (7.5 g, 45.26 mmol) was added to a mixture of (2R,5R)-5- hydroxymethyl-2-methyl-piperazine- 1 -carboxylic acid teit-butyl ester (5.7 g, 24.89 mmol), 2- chloro- 1 -[6-(4-fluorobenzyl)-3, 3-dimethyl-2, 3-dihydro-pyrrolo[3,2-b]pyridin- 1 -yl]-ethanone hydrochloride (8.35 g, 22.63 mmol) potassium carbonate (12.5 g, 90.51 mmol) and acetonitrile (100 mL) under nitrogen. The mixture was stirred at 20 C overnight. The mixture waspartitioned between water (300 mL) and EtOAc (300 mL) and the organic phase was dried and evaporated in vacuo to give the title compound (12.14 g). MS: [M+H] = 527.
12.14 g With potassium carbonate; potassium iodide; In acetonitrile; at 20℃;Inert atmosphere; Preparation 18: (2R,5R)-4-{2-[6-(4-FI uoro-benzyl)-3,3-di methyl-2,3-di hydro-pyrrolo[3,2- b]pyridi n-I -yI]-2-oxo-ethyl}-5-hydroxymethyl-2-methyl-pi perazi ne-I -carboxylic acid tert-butyl esterFinely ground potassium iodide (7.5 g, 45.26 mmol) was added to a mixture of (2R,5R)-5-hydroxymethyl-2-methyl-piperazine-1-carboxylic acid teit-butyl ester (5.7 g, 24.89 mmol), 2-chloro- 1 -[6-(4-fluorobenzyl)-3, 3-dimethyl-2, 3-dihydro-pyrrolo[3,2-b]pyridin- 1 -yl]-ethanone hydrochloride (8.35 g, 22.63 mmol) potassium carbonate (12.5 g, 90.51 mmol) and acetonitrile (100 mL) under nitrogen. The mixture was stirred at 20 00 overnight. The mixture was partitioned between water (300 mL) and EtOAc (300 mL) and the organic phasewas dried and evaporated in vacuo to give the title compound (12.14 g). MS: [M+H] = 527.
  • 16
  • [ 1403898-64-5 ]
  • [ 1605312-01-3 ]
  • 17
  • [ 1403898-64-5 ]
  • [ 1605312-81-9 ]
  • 18
  • [ 1403898-64-5 ]
  • [ 1605311-64-5 ]
  • 19
  • [ 1403898-64-5 ]
  • 1-[(2R,5R)-1-(2-{6-[(4-fluorophenyl)methyl]-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl}-2-oxoethyl)-5-methylpiperazin-2-yl]methyl}-4,4-dimethylpyrrolidin-2-one dihydrochloride [ No CAS ]
  • 20
  • [ 1403898-64-5 ]
  • [ 1605311-65-6 ]
  • 21
  • [ 1403898-64-5 ]
  • [ 1605311-66-7 ]
  • 22
  • [ 1403898-64-5 ]
  • [ 613-45-6 ]
  • [ 1605312-93-3 ]
YieldReaction ConditionsOperation in experiment
99% With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; Preparation 46: (2R,5R) -4-(2,4-Di methoxy-benzyl)-5-hydroxymethyl-2-methyl-pi perazi ne1-carboxylic acid tert-butyl ester To an ice-cooled solution of (2R ,5R)-5-hydroxymethyl-2-methyl-piperazine- 1 -carboxylic acid tert-butyl ester (10.0 g, 43.5 mmol) in DOE (70 mL) were added 2,4-dimethoxy-benzaldehyde (11.1 g, 66.6 mmol) and sodium triacetoxyborohydride(11.1 g, 52.2 mmol) in small portions. Thereaction mixture was stirred at room temperature overnight. Saturated aqueous NaHCO3 was added and the product was extracted with DCM. The organic phase was dried and evaporated. Chromatography on silica gel, eluting with petrol - EtOAc 0-50% gave the title compound (16.3 g, 99%). 1297-012-1 MS: [M+H] = 381.
  • 23
  • [ 24424-99-5 ]
  • [ 1403898-63-4 ]
  • [ 1403898-64-5 ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine; In methanol; at 0 - 50℃; for 20.5h; Preparation 4: (2R,5R)-5-Hydroxymethyl-2-methyl-pi perazi ne-I -carboxylic acid tertbutyl esterTo ((2R,5R)-5-methyl-piperazin-2-yl)-methanol hydrochloride (20 g, 119 mmol) in MeOH (96 mL) at 0 C (ice bath) was added triethylamine (48.7 mL, 357 mmol). teit-Butyl dicarbonate (61 g, 280 mmol) in MeOH (145 mL) was added over 30 mm. The reaction temperature was maintained at <10 c for 1 h, warmed to ambient temperature over 1 h and then heated to 50 00 for 18 h. The reaction was concentrated and the residue dissolved in ethanol (397 mL). Asolution of NaOH (23.8 g, 595 mmol) in water (397 mL) was added and the reaction heated to 100 00 for 18 h, then cooled to ambient temperature. Mixture was neutralised with 1M HCI (-300 mL) to pH 9 (using a pH meter), then extracted with chloroform (3 x 700 mL), dried over sodium sulfate, filtered and concentrated. The residue was redissolved in MeOH and concentrated, then dried in vacuo at 40 c to give the title compound (21 g, 75%) as acolourless solid. 1H NMR (Me-d3-OD): 4.20-4.07 (1H, m), 3.79 (1H, dd), 3.71-3.58 (2H, m),3.54 (1H, dd), 3.24 (1H, dd), 3.18-3.01 (1H, m), 3.01-2.89 (1H, m), 2.55 (1H, dd), 1.48 (9H,5), 1.25 (3H, 5).
  • 24
  • [ 1403898-64-5 ]
  • [ 1605317-72-3 ]
  • 25
  • [ 1403898-64-5 ]
  • [ 1605317-73-4 ]
  • 26
  • [ 1403898-64-5 ]
  • [ 1605317-80-3 ]
  • 27
  • [ 1403898-64-5 ]
  • (2R,5S)-5-[(2R,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-morpholin-4-yl methyl]-4-{2-[6-(4-fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-oxo-ethyl}-2-methyl-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 28
  • [ 1403898-64-5 ]
  • 2-[(2R,5R)-2-[(3R,5R)-3,5-dimethylmorpholin-4-yl]methyl}-5-methylpiperazin-1-yl]-1-{6-[(4-fluorophenyl)methyl]-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl}ethan-1-one dihydrochloride [ No CAS ]
  • 29
  • [ 1403898-64-5 ]
  • [ 1605317-28-9 ]
  • 30
  • [ 1403898-64-5 ]
  • (2R,5S)-2-methyl-5-((R)-3-methyl-morpholin-4-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 31
  • [ 1403898-64-5 ]
  • 1-{6-[(4-fluorophenyl)methyl]-5-(hydroxymethyl)-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl}-2-[(2R,5R)-5-methyl-2-[(3R)-3-methylmorpholin-4-yl]methyl}piperazin-1-yl]ethan-1-one dihydrochloride [ No CAS ]
  • 32
  • [ 1403898-64-5 ]
  • tert-butyl (2R,5S)-4-(2-{6-[(4-fluorophenyl)methyl]-5-(hydroxymethyl)-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl}-2-oxoethyl)-2-methyl-5-[(3R)-3-methylmorpholin-4-yl]methyl}piperazine-1-carboxylate [ No CAS ]
  • 33
  • [ 1403898-64-5 ]
  • 1-{6-[(4-fluorophenyl)methyl]-5-(hydroxymethyl)-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl}-2-[(2R,5R)-5-methyl-2-[(3R)-3-methylmorpholin-4-yl]methyl}piperazin-1-yl]ethan-1-one [ No CAS ]
  • 34
  • [ 1403898-64-5 ]
  • 1-{6-[(4-fluorophenyl)methyl]-5-(hydroxymethyl)-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl}-2-[(2R,5R)-5-methyl-2-[(3R)-3-methylmorpholin-4-yl]methyl}piperazin-1-yl]ethan-1-one L(+)-lactate [ No CAS ]
  • 35
  • [ 1403898-64-5 ]
  • 1-{6-[(4-fluorophenyl)methyl]-5-(hydroxymethyl)-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl}-2-[(2R,5R)-5-methyl-2-[(3R)-3-methylmorpholin-4-yl]methyl}piperazin-1-yl]ethan-1-one sulfate [ No CAS ]
  • 36
  • [ 1403898-64-5 ]
  • 1-{6-[(4-fluorophenyl)methyl]-5-(hydroxymethyl)-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl}-2-[(2R,5R)-5-methyl-2-[(3R)-3-methylmorpholin-4-yl]methyl}piperazin-1-yl]ethan-1-one [ No CAS ]
  • 37
  • [ 1403898-64-5 ]
  • (2R,5S)-4-benzyl-2-methyl-5-((R)-3-methyl-morpholin-4-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 38
  • [ 1403898-64-5 ]
  • (2R,5R)-4-[2-(6-chloro-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridin-1-yl)-2-oxo-ethyl]-5-methoxymethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 39
  • [ 1403898-64-5 ]
  • [ 1403900-65-1 ]
  • 40
  • [ 1403898-64-5 ]
  • 1-(6-chloro-3,3-dimethyl-2,3-dihydro-1H-indol-1-yl)-2-[(2R,5R)-2-(methoxymethyl)-5-methylpiperazin-1-yl]ethan-1-one [ No CAS ]
  • 41
  • [ 1403898-64-5 ]
  • 1-{6-chloro-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-c]pyridin-1-yl}-2-[(2R,5R)-2-(methoxymethyl)-5-methylpiperazin-1-yl]ethan-1-one [ No CAS ]
  • 42
  • [ 1403898-64-5 ]
  • [ 1403896-55-8 ]
  • 43
  • [ 1403898-64-5 ]
  • [ 1403898-74-7 ]
  • 44
  • [ 1403898-64-5 ]
  • [ 1403898-72-5 ]
  • 45
  • [ 1403898-64-5 ]
  • [ 1403898-73-6 ]
  • 46
  • [ 1403898-64-5 ]
  • [ 501-53-1 ]
  • [ 1403898-71-4 ]
  • 47
  • [ 1403898-64-5 ]
  • 2-chloro-1-[6-(4-fluorobenzyl)-3,3-dimethyl-2,3-dihydropyrrolo[3,2-b]pyridin-1-yl]ethanone hydrochloride [ No CAS ]
  • [ 1403903-27-4 ]
  • 48
  • [ 1403898-64-5 ]
  • C18H17ClF2N2O [ No CAS ]
  • (2R,5R)-4-{2-[6-(2,4-difluorobenzyl)-3,3-dimethyl-2,3-dihydropyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl}-5-hydroxymethyl-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 49
  • [ 1403898-64-5 ]
  • (2R,5S)-4-{2-[6-(4-fluorobenzyl)-3,3-dimethyl-2,3-dihydropyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl}-2-methyl-5-((S)-3-methylmorpholin-4-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 50
  • [ 1403898-64-5 ]
  • (2R,5R)-5-chloromethyl-4-{2-[6-(2,4-difluorobenzyl)-3,3-dimethyl-2,3-dihydropyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl}-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 51
  • [ 1403898-64-5 ]
  • (2R,5S)-4-{2-[6-(2,4-difluorobenzyl)-3,3-dimethyl-2,3-dihydropyrrolo[3,2-c]pyridin-1-yl]-2-oxoethyl}-2-methyl-5-morpholin-4-ylmethylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 52
  • [ 1403898-64-5 ]
  • (2R,5S)-4-{2-[6-(2,4-difluorobenzyl)-3,3-dimethyl-2,3-dihydropyrrolo[3,2-c]pyridin-1-yl]-2-oxoethyl}-2-methyl-5-pyrrolidin-1-ylmethylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 53
  • [ 1403898-64-5 ]
  • 1-{6-benzyl-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-c]pyridin-1-yl}-2-[(2R,5R)-5-methyl-2-[(4-methyl-1H-pyrazol-1-yl)methyl]piperazin-1-yl]ethan-1-one hydrochloride [ No CAS ]
  • 54
  • [ 1403898-64-5 ]
  • 1-{6-benzyl-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl}-2-[(2R,5R)-2-[(4-fluoro-1Hpyrazol-1-yl)methyl]-5-methylpiperazin-1-yl]ethan-1-one hydrochloride [ No CAS ]
  • 55
  • [ 1403898-64-5 ]
  • 1-[(2R,5R)-1-(2-{6-benzyl-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl}-2-oxoethyl)-5-methylpiperazin-2-yl]methyl}pyrrolidin-2-one hydrochloride [ No CAS ]
  • 56
  • [ 1403898-64-5 ]
  • 1-[(2R,5R)-1-(2-{6-[(4-fluorophenyl)methyl]-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl}-2-oxoethyl)-5-methylpiperazin-2-yl]methyl}pyrrolidin-2-one hydrochloride [ No CAS ]
  • 57
  • [ 1403898-64-5 ]
  • 1-[(2R,5R)-1-(2-{6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl}-2-oxoethyl)-5-methylpiperazin-2-yl]methyl}pyrrolidin-2-one hydrochloride [ No CAS ]
  • 58
  • [ 1403898-64-5 ]
  • 1-[(2R,5R)-1-(2-{6-[difluoro(phenyl)methyl]-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl}-2-oxoethyl)-5-methylpiperazin-2-yl]methyl}pyrrolidin-2-one hydrochloride [ No CAS ]
  • 59
  • [ 1403898-64-5 ]
  • 1-[(2R,5R)-1-{2-[6-(1,1-difluoroethyl)-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl}-5-methylpiperazin-2-yl]methyl}pyrrolidin-2-one hydrochloride [ No CAS ]
  • 60
  • [ 1403898-64-5 ]
  • 1-[(2R,5R)-1-{2-[6-(1,1-difluoropropyl)-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl}-5-methylpiperazin-2-yl]methyl}pyrrolidin-2-one hydrochloride [ No CAS ]
  • 61
  • [ 1403898-64-5 ]
  • 1-[(2R,5R)-1-{2-[6-(1,1-difluorobutyl)-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl}-5-methylpiperazin-2-yl]methyl}pyrrolidin-2-one hydrochloride [ No CAS ]
  • 62
  • [ 1403898-64-5 ]
  • 1-[(2R,5R)-1-(2-{6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-c]pyridin-1-yl}-2-oxoethyl)-5-methylpiperazin-2-yl]methyl}pyrrolidin-2-one hydrochloride [ No CAS ]
  • 63
  • [ 1403898-64-5 ]
  • 1-{6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-c]pyridin-1-yl}-2-[(2R,5R)-5-methyl-2-(pyrrolidin-1-ylmethyl)piperazin-1-yl]ethan-1-one dihydrochloride [ No CAS ]
  • 64
  • [ 1403898-64-5 ]
  • 1-{6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-c]pyridin-1-yl}-2-[(2R,5R)-2-[(3S)-3-fluoropyrrolidin-1-yl]methyl}-5-methylpiperazin-1-yl]ethan-1-one dihydrochloride [ No CAS ]
  • 65
  • [ 1403898-64-5 ]
  • 1-{6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-c]pyridin-1-yl}-2-[(2R,5R)-2-[(3R)-3-fluoropyrrolidin-1-yl]methyl}-5-methylpiperazin-1-yl]ethan-1-one dihydrochloride [ No CAS ]
  • 66
  • [ 1403898-64-5 ]
  • 1-{6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-c]pyridin-1-yl}-2-[(2R,5R)-5-methyl-2-(morpholin-4-ylmethyl)piperazin-1-yl]ethan-1-one dihydrochloride [ No CAS ]
  • 67
  • [ 1403898-64-5 ]
  • 1-{6-[(4-fluorophenyl)methyl]-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl}-2-[(2R,5R)-5-methyl-2-[(morpholin-4-yl)methyl]piperazin-1-yl]ethan-1-one hydrochloride [ No CAS ]
  • 68
  • [ 1403898-64-5 ]
  • 1-{6-[(4-fluorophenyl)methyl]-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-1-yl}-2-[(2R,5R)-5-methyl-2-[(3S)-3-methylmorpholin-4-yl]methyl}piperazin-1-yl]ethan-1-one hydrochloride [ No CAS ]
  • 69
  • [ 1403898-64-5 ]
  • [ 1403904-77-7 ]
  • 70
  • [ 1403898-64-5 ]
  • 1-{6-[(4-fluorophenyl)methyl]-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]-pyridin-1-yl}-2-[(2R,5R)-5-methyl-2-[(3R)-3-methylmorpholin-4-yl]-methyl}piperazin-1-yl]ethan-1-one hydrochloride [ No CAS ]
  • 71
  • [ 1403898-64-5 ]
  • (2R,5S)-4-benzyl-2-methyl-5-(2-oxopyrrolidin-1-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 72
  • [ 1403898-64-5 ]
  • (2R,5S)-2-methyl-5-(2-oxopyrrolidin-1-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 73
  • [ 1403898-64-5 ]
  • (2R,5S)-4-benzyloxycarbonylmethyl-2-methyl-5-(2-oxopyrrolidin-1-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 74
  • [ 1403898-64-5 ]
  • (2R,5S)-4-carboxymethyl-2-methyl-5-(2-oxopyrrolidin-1-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 75
  • [ 1403898-64-5 ]
  • (2R,5S)-4-benzyl-2-methyl-5-morpholin-4-ylmethylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 76
  • [ 1403898-64-5 ]
  • (2R,5S)-4-benzyl-5-((S)-3-fluoropyrrolidin-1-ylmethyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 77
  • [ 1403898-64-5 ]
  • (2R,5S)-4-benzyl-5-((R)-3-fluoropyrrolidin-1-ylmethyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 78
  • [ 1403898-64-5 ]
  • (2R,5S)-2-methyl-5-morpholin-4-ylmethylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 79
  • [ 1403898-64-5 ]
  • (2R,5S)-5-((S)-3-fluoropyrrolidin-1-ylmethyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 80
  • [ 1403898-64-5 ]
  • (2R,5S)-5-((R)-3-fluoropyrrolidin-1-ylmethyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 81
  • [ 1403898-64-5 ]
  • (2R,5S)-4-benzyloxycarbonylmethyl-2-methyl-5-morpholin-4-ylmethylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 82
  • [ 1403898-64-5 ]
  • (2R,5S)-4-carboxymethyl-2-methyl-5-morpholin-4-ylmethylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 83
  • [ 1403898-64-5 ]
  • C19H30N2O5S [ No CAS ]
  • 84
  • [ 1403898-64-5 ]
  • (2R,5R)-4-benzyl-5-(4-fluoro-pyrazol-1-ylmethyl)-2-methyl-piperazine-1-carboxylic acid tertbutyl ester [ No CAS ]
  • 85
  • [ 1403898-64-5 ]
  • (2R,5R)-4-benzyl-2-methyl-5-(4-methylpyrazol-1-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 86
  • [ 1403898-64-5 ]
  • (2R,5R)-5-(4-fluoropyrazol-1-ylmethyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester acetate [ No CAS ]
  • 87
  • [ 1403898-64-5 ]
  • (2R,5R)-5-(4-methylpyrazol-1-ylmethyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester acetate [ No CAS ]
  • 88
  • [ 1403898-64-5 ]
  • (2R,5R)-4-benzyloxycarbonylmethyl-5-(4-fluoropyrazol-1-ylmethyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 89
  • [ 1403898-64-5 ]
  • (2R,5R)-4-benzyloxycarbonylmethyl-2-methyl-5-(4-methylpyrazol-1-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 90
  • [ 1403898-64-5 ]
  • (2R,5R)-4-carboxymethyl-5-(4-fluoropyrazol-1-ylmethyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 91
  • [ 1403898-64-5 ]
  • (2R,5R)-4-carboxymethyl-5-(4-methylpyrazol-1-ylmethyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 92
  • [ 1403898-64-5 ]
  • (2R,5R)-4-[2-(6-benzyl-3,3-dimethyl-2,3-dihydropyrrolo[3,2-b]pyridin-1-yl)-2-oxoethyl]-5-(4-fluoropyrazol-1-ylmethyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 93
  • [ 1403898-64-5 ]
  • (2R,5S)-4-[2-(6-benzyl-3,3-dimethyl-2,3-dihydropyrrolo[3,2-b]pyridin-1-yl)-2-oxoethyl]-2-methyl-5-(2-oxopyrrolidin-1-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 94
  • [ 1403898-64-5 ]
  • tert-butyl (2R,5S)-4-(2-{6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-c]pyridin-1-yl}-2-oxoethyl)-5-[(3S)-3-fluoropyrrolidin-1-yl]methyl}-2-methylpiperazine-1-carboxylate hydrochloride [ No CAS ]
  • 95
  • [ 1403898-64-5 ]
  • tert-butyl (2R,5S)-4-(2-{6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-c]pyridin-1-yl}-2-oxoethyl)-5-[(3R)-3-fluoropyrrolidin-1-yl]methyl}-2-methylpiperazine-1-carboxylate hydrochloride [ No CAS ]
  • 96
  • [ 1403898-64-5 ]
  • (2R,5S)-4-{2-[6-(1,1-difluoropropyl)-3,3-dimethyl-2,3-dihydropyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl}-2-methyl-5-(2-oxopyrrolidin-1-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
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