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Product Details of [ 1211539-85-3 ]

CAS No. :1211539-85-3 MDL No. :MFCD18261120
Formula : C8H5ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LBDBVFSANWWOHH-UHFFFAOYSA-N
M.W : 196.59 Pubchem ID :82399232
Synonyms :

Calculated chemistry of [ 1211539-85-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 48.06
TPSA : 65.98 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.0
Log Po/w (XLOGP3) : 1.47
Log Po/w (WLOGP) : 1.91
Log Po/w (MLOGP) : 0.49
Log Po/w (SILICOS-IT) : 2.0
Consensus Log Po/w : 1.38

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -2.43
Solubility : 0.728 mg/ml ; 0.0037 mol/l
Class : Soluble
Log S (Ali) : -2.46
Solubility : 0.678 mg/ml ; 0.00345 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.9
Solubility : 0.245 mg/ml ; 0.00124 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 1211539-85-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1211539-85-3 ]

* 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 [ 1211539-85-3 ]

[ 1211539-85-3 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 1211539-85-3 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 0.5 h / 30 °C 1.2: 11.5 h / 30 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 30 °C
  • 2
  • [ 1211539-85-3 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
60.95% Stage #1: 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 30℃; for 0.5h; Stage #2: (1S,2S,3S,5R)-(+)-isopinocampheylamine In N,N-dimethyl-formamide at 30℃; for 11.5h; 39 Example 39. MPL-006 Synthesis of 4-chloro-N-[(1S,2S,3S,5R)-2,6,6-trimethylnorpinan-3-yl]-1H-pyrrolo[2,3- c]Pyridine -2-carboxamide To a solution of 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (250 mg, 1.27 mmol, 1 eq) in DMF (3 mL) was added CDI (268.06 mg, 1.65 mmol, 1.3 eq). The mixture was stirred at 30 °C for 0.5 h. Then (1S,2S,3S,5R)-2,6,6-trimethylnorpinan-3-amine (292.35 mg, 1.91 mmol, 1.5 eq) was added. The mixture was stirred at 30 °C for 11.5 h. LCMS showed there was no starting material. The reaction was added dropwise to H2O (20 mL). There was much precipitation which was collected by filter. The cake was diluted with EtOAc(30 mL), dried with anhydrous MgSO4, filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography (SiO2, Petroleum ether:EtOAc = 1:1). Compound 4- chloro-N-[(1S,2S,3S,5R)-2,6,6-trimethylnorpinan-3-yl]-1H-pyrrolo[2,3-c]pyridine-2- carboxamide (259 mg, 775.07 umol, 60.95% yield, 99.305% purity) was obtained as a white solid. LCMS (ESI), m/z 331.15[M+H] + ; 1H NMR (400MHz, DMSO-d6) = 12.46 (br s, 1H), 8.74 (s, 1H), 8.71 (br d, J=8.6 Hz, 1H), 8.19 (s, 1H), 7.39 (s, 1H), 4.46 - 4.35 (m, 1H), 2.48 - 2.35 (m, 2H), 2.10 (br t, J=7.2 Hz, 1H), 2.01 - 1.92 (m, 1H), 1.83 (br t, J=5.1Hz, 1H), 1.72 (br dd, J=6.4, 11.7 Hz, 1H), 1.27 - 1.20 (m, 4H), 1.11 - 1.05 (m, 6H).
  • 3
  • [ 20615-18-3 ]
  • [ 1211539-85-3 ]
  • [ 2637386-53-7 ]
YieldReaction ConditionsOperation in experiment
55.14% Stage #1: 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 30℃; for 2.5h; Stage #2: 4,4-dimethyl-1-cyclohexylamine In N,N-dimethyl-formamide at 30℃; for 0.5h; 38 Example 38. MPL-003 Synthesis of 4-chloro-N-(4,4-dimethylcyclohexyl)-1H-pyrrolo[2,3-c]pyridine-2- carboxamide To a solution of 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (800 mg, 4.07 mmol, 1 eq) in DMF (8 mL) was added CDI (989.77 mg, 6.10 mmol, 1.5 eq), the mixture was stirred at 30 °C for 2.5h, then 4,4-dimethylcyclohexanamine (776.60 mg, 6.10 mmol, 1.5 eq) was added. The mixture was stirred at 30 °C for another 0.5 h. LC-MS showed 20 % of the starting material 4 was remained and one main peak with desired mass was detected. The mixture was added to water (100mL), filtered and the filter cake was washed with 20 mL x 3 of Petroleum ether, dried under reduced pressure to give the product. The product 4-chloro-N-(4,4-dimethylcyclohexyl)- 1H-pyrrolo[2,3-c] pyridine-2-carboxamide (692.4 mg, 2.24 mmol, 55.14% yield, 99.104% purity) was obtained as white solid. LCMS (ESI) m/z 306.1 [M+H] +; 1H NMR (400MHz, DMSO-d6) = 12.43 (br s, 1H), 8.72 (s, 1H), 8.59 (br d, J=7.6 Hz, 1H), 8.18 (s, 1H), 7.33 (s, 1H), 3.76 (br d, J=6.6 Hz, 1H), 1.67 (br d, J=10.3 Hz, 2H), 1.60 - 1.50 (m, 2H), 1.45 - 1.37 (m, 2H), 1.34 - 1.24 (m, 2H), 0.94 (br d, J=9.0 Hz, 6H).
  • 4
  • [ 4481-88-3 ]
  • [ 1211539-85-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
77.45% Stage #1: 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 25℃; for 0.5h; Stage #2: bornylamine In N,N-dimethyl-formamide at 25℃; for 11.5h; 107 Example 107. MPL-189 Synthesis of 4-chloro-N-(1,7,7-trimethylnorbornan-2-yl)-1H-pyrrolo[2,3-c]pyridine-2- Carboxamide To a solution of 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (150 mg, 763.01 umol, 1 eq) and CDI (148.46 mg, 915.61 umol, 1.2 eq) in DMF (5 mL). The mixture was stirred at 25 °C for 0.5 h. 1,7,7-trimethylnorbornan-2-amine (140.33 mg, 915.61 umol, 1.2 eq) was added. The mixture was stirred at 25 °C for 11.5 h. LCMS showed no starting material. The reaction mixture was added to water (20 ml), filtered and the filter cake was washed with 10 mL of water, dried in vacuo to give product. The residue was diluted in CH3CN (5 mL) and H2O (20 mL) and then lyophilized. The product 4-chloro-N-(1,7,7-trimethylnorbornan-2-yl)-1H-pyrrolo [2,3- c]pyridine-2-carboxamide (196.1 mg, 590.95 umol, 77.45% yield, 100% purity) was obtained as white solid. LCMS (ESI) m/z 332.2 [M+H]+; 1H NMR (500MHz, DMSO-d6) d = 12.44 (br s, 1H), 8.73 (s, 1H), 8.42 (br d, J=8.5 Hz, 1H), 8.19 (s, 1H), 7.51 (s, 1H), 4.45 - 4.37 (m, 1H), 2.24 - 2.15 (m, 1H), 1.78 (ddd, J=4.1, 9.1, 13.0 Hz, 1H), 1.74 - 1.65 (m, 2H), 1.43 (dt, J=4.0, 10.3 Hz, 1H), 1.27 (br t, J=11.6 Hz, 1H), 1.19 (dd, J=5.0, 12.9 Hz, 1H), 0.97 (s, 3H), 0.87 (s, 3H), 0.78 (s, 3H).
  • 5
  • [ 1211539-85-3 ]
  • [ 61888-92-4 ]
  • [ 2637387-37-0 ]
YieldReaction ConditionsOperation in experiment
13.58% Stage #1: 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 30℃; for 0.5h; Inert atmosphere; Stage #2: 4,4-dimethylcyclohex-2-en-1-amine In N,N-dimethyl-formamide at 30℃; for 2h; Inert atmosphere; 102 Example 102. MPL-169 4-chloro-N-(4,4-dimethylcyclohex-2-en-1-yl)-1H-pyrrolo[2,3-c]pyridine -2-carboxamide To a solution of 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (50 mg, 254.34 umol, 1 eq) in DMF (1 mL) was added CDI (82.48 mg, 508.67 umol, 2 eq) under N2 atmosphere. The mixture was stirred at 30 °C for 0.5 hr under N2 atmosphere. Then 4,4-dimethylcyclohex-2-en- 1-amine (38.21 mg, 305.20 umol, 1.2 eq) was added. The mixture was stirred at 30 °C for 2 hr under N2 atmosphere. LCMS showed there was no starting material and main desired compound. The mixture was added in water (10mL) and stirred for 10 mins. The mixture was extracted with EtOAc (15 mL x 3). The mixture was dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by reversed-phase HPLC(column: YMC- Actus Triart C18150*30mm*5um; mobile phase: [water(0.1%TFA)-ACN];B%: 65%- 83%,9min). Compound 4-chloro-N-(4,4-dimethylcyclohex-2-en-1-yl)- 1H-pyrrolo[2,3- c]pyridine-2-carboxamide (10.6 mg, 34.54 umol, 13.58% yield, 99% purity) was obtained as a white solid. LCMS (ESI) m/z 304.1 [M+H] +; 1H NMR (400 MHz, DMSO-d6) d =0.95 - 1.10 (m, 6 H) 1.23 (br s, 1H) 1.42 - 1.53 (m, 1H) 1.56 - 1.75 (m, 2 H) 1.86 (br d, J=3.91Hz, 1H) 4.49 (br d, J=5.62 Hz, 1H) 5.47 (dd, J=10.03, 2.45 Hz, 1H) 5.55 - 5.61 (m, 1H) 7.42 (s, 1H) 8.18 (s, 1H) 8.73 (s, 1H) 8.78 (br d, J=8.07 Hz, 1H) 12.49 (br s, 1H).
  • 6
  • [ 1211539-85-3 ]
  • [ 2637388-83-9 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 80℃; for 0.5h; Inert atmosphere; 50 Synthesis of 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl chloride To a solution of 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (100 mg, 508.67 umol, 1 eq) in DCM (5 mL) was added oxalyl dichloride (645.64 mg, 5.09 mmol, 445.27 uL, 10 eq) and DMF (1.12 mg, 15.26 umol, 1.17 uL, 0.03 eq) under N2, The mixture was stirred at 80 °C for 0.5 hr. LC-MS showed the starting material 4 was consumed completely and one main peak with desired mass was detected. The mixture was concentrated under reduced pressure to give a residue. The crude product 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl chloride (109 mg, 506.89 umol, 99.65% yield) was obtained as yellow solid and used directly for the next step without purification. LCMS (ESI) m/z 211.0 [M-Cl+OMe] +
  • 7
  • [ 1211539-85-3 ]
  • [ 2637386-70-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 80 °C / Inert atmosphere 2: triethylamine / dichloromethane / 0.5 h / 25 °C / Inert atmosphere
  • 8
  • [ 1211539-85-3 ]
  • [ 23263-48-1 ]
  • [ 2637386-22-0 ]
YieldReaction ConditionsOperation in experiment
25.89% With 1-methyl-1H-imidazole; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate In N,N-dimethyl-formamide at 30℃; for 12h; 23 Example 23. MPL-166 Synthesis of N-(3-bicyclo[3.2.1]octanyl)-4-chloro-1H-pyrrolo[2,3-c]pyridine-2- carboxamide To a solution of 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (50 mg, 254.34 umol, 1 eq) in DMF (1 mL) was added bicyclo[3.2.1]octan-3-amine (49.34 mg, 305.20 umol, 1.2 eq, HCl), 1-methylimidazole (83.53 mg, 1.02 mmol, 81.09 uL, 4 eq) and [chloro(dimethylamino)methylene]-dimethyl-ammonium;hexafluorophosphate (92.77 mg, 330.64 umol, 1.3 eq). The mixture was stirred at 30 °C for 12 hr. LCMS showed there were no starting material and main desired compound. The reaction was added dropwise to H2O (20 mL). There was much precipitation which was collected by filter. The cake was diluted in EtOAc (20 mL), dried with anhydrous MgSO4, filtered. The filtrate was concentrated in vacuo. The residue was purified by prep-HPLC (column: YMC-Actus Triart C18150*30mm*5um; mobile phase: [water(0.225%FA)-ACN]; B%: 30%-58%,11min). Compound N-(3- bicyclo[3.2.1]octanyl)-4-chloro-1H-pyrrolo[2,3-c] pyridine-2-carboxamide (20 mg, 65.84 umol, 25.89% yield, 100% purity) was obtained as a white solid. LCMS (ESI) m/z 304.1 [M+H]+ ; 1H NMR (400MHz, DMSO-d6) d =12.48 (br s, 1H), 8.73 (s, 1H), 8.53 (br d, J=6.8 Hz, 1H), 8.19 (s, 1H), 7.32 (s, 1H), 4.20 - 4.07 (m, 1H), 2.24 (br s, 2H), 1.73 (br d, J=12.2 Hz, 2H), 1.69 - 1.58 (m, 2H), 1.52 (br d, J=7.6 Hz, 2H), 1.46 - 1.32 (m, 4H).
  • 9
  • [ 1330276-94-2 ]
  • [ 1211539-85-3 ]
  • [ 2637387-46-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 25℃; for 0.5h; Stage #2: 1,1-dimethylsilinan-4-amine In N,N-dimethyl-formamide at 30℃; for 11.5h; 109 Example 109. MPL-192 Synthesis of 4-chloro-N-(1,1-dimethylsilinan-4-yl)-1H-pyrrolo [2,3-c]pyridine-2-carboxamide To a solution of 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (150 mg, 763.01 umol, 1 eq) in DMF (4 mL) was added CDI (160.84 mg, 991.91 umol, 1.3 eq). The mixture was stirred at 25 °C for 0.5 h. Then 1,1-dimethylsilinan-4-amine (142.14 mg, 991.91 umol, 1.3 eq) was added. The mixture was stirred at 30 °C for 11.5 h. LCMS showed there was no starting material. The reaction was added dropwise to H2O (20 mL). There was much precipitation which was collected by filter. The cake was diluted with EtOAc (30 mL), dried with anhydrous MgSO4, filtered. The filtrate was concentrated in vacuo. The residue was diluted in CH3CN (5 mL) and H2O (20 mL) lyophilized without further purification. Compound 4-chloro-N-(1,1- dimethylsilinan-4-yl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (116.2 mg, 342.06 umol, 44.83% yield, 94.75% purity) was obtained as a white solid. LCMS (ESI), m/z 322.1[M+H] +; 1H NMR (500MHz, CHLOROFORM-d) = 10.78 (br s, 1H), 8.85 (s, 1H), 8.32 - 8.28 (m, 1H), 6.93 (d, J=1.5 Hz, 1H), 6.28 (br d, J=7.9 Hz, 1H), 4.04 - 3.95 (m, 1H), 2.28 - 2.21 (m, 2H), 1.70 - 1.63 (m, 2H), 1.29 - 1.25 (m, 1H), 0.89 - 0.71 (m, 4H), 0.10 (d, J=16.5 Hz, 6H).
  • 10
  • [ 1211539-85-3 ]
  • [ 168286-10-0 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
37.24% Stage #1: 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 30℃; for 0.5h; Stage #2: (1R,2R,3S,5R)-3-amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol In N,N-dimethyl-formamide at 30℃; for 11.5h; 32 Example 32. MPL-222 Synthesis of 4-chloro-N-[(1R, 2R, 3S, 5R)-2-hydroxy-2,6,6-trimethyl-norpinan-3-yl]-1H-Pyrrolo [2,3-c]pyridine-2-carboxamide To a solution of 4-chloro-1H-pyrrolo [2, 3-c] pyridine-2-carboxylic acid (50 mg, 254.34 umol, 1 eq) DMF (1.5 mL) was added CDI (45.36 mg, 279.77 umol, 1.1 eq). The mixture was stirred at 30 °C for 0.5 h. Then (1R, 2R, 3S, 5R)-3-amino-2, 6, 6-trimethyl-norpinan-2-ol (45.20 mg, 267.05 umol, 1.05 eq) was added. The mixture was stirred at 30 °C for 11.5 h. LCMS showed there was no starting material. The reaction was added dropwise to H2O (20 mL). There was much precipitation which was collected by filter. The cake was transfered in bottom flask. The residue was purified by prep-HPLC (column: YMC-Actus Triart C18100*30mm*5um; mobile phase: [water (0.225%FA)-ACN];B%:25%-55%,11min)Compound 4-chloro-N-[(1R,2R,3S,5R)-2-hydroxy -2, 6, 6-trimethyl-norpinan-3-yl]-1H-pyrrolo [2,3-c]pyridine-2-carboxamide (33 mg, 94.72 umol, 37.24% yield, 99.840% purity) was obtained as a white solid. LCMS (ESI), m/z 348.0[M+H] + 1H NMR (500MHz, CDCl3) = 10.58 (br s, 1H), 8.85 (s, 1H), 8.28 (s, 1H), 7.53 (br d, J=7.5 Hz, 1H), 7.01 (s, 1H), 4.61 - 4.55 (m, 1H), 2.78 -2.71 (m, 1H), 2.37 - 2.28 (m, 1H), 2.11 - 2.05 (m, 2H), 1.68 (br dd, J=6.2, 13.0 Hz, 1H), 1.49 (d, J=10.5 Hz, 1H), 1.41 (s, 3H), 1.35 (s, 3H), 1.16 (s, 3H).
  • 11
  • [ 1211539-85-3 ]
  • [ 1256256-54-8 ]
  • [ 2637387-33-6 ]
YieldReaction ConditionsOperation in experiment
35.42% With 1-methyl-1H-imidazole; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate In N,N-dimethyl-formamide at 30℃; for 12h; 99 Example 99. MPL-163 Synthesis of 4-chloro-N-spiro[2.5]octan-6-yl-1H-pyrrolo[2,3-c]pyridine-2-carboxamide To a solution of spiro[2.5]octan-6-amine (53.85 mg, 333.08 umol, 1.2 eq, HCl) in DMF (1 mL) was added 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (54.57 mg, 277.57 umol, 1 eq), 1-methylimidazole (91.15 mg, 1.11 mmol, 88.50 uL, 4 eq) and [chloro(dimethylamino)methylene] -dimethyl-ammonium;hexafluorophosphate (116.82 mg, 416.35 umol, 1.5 eq). The mixture was stirred at 30 °C for 12 hr. LCMS showed there were starting material and main desired compound. The reaction was added dropwise to H2O (20 mL). There was much precipitation which was collected by filter. The cake was diluted in EtOAc (20 mL) and concentrated in vacuo. The residue was purified by prep-HPLC (column: YMC-Actus Triart C18150*30mm*5um; mobile phase: [water(0.225%FA)-ACN];B%: 31%- 60%,11min). Compound 4-chloro-N-spiro[2.5]octan-6-yl-1H- pyrrolo[2,3-c]pyridine-2- carboxamide (30 mg, 98.32 umol, 35.42% yield, 99.56% purity) was obtained as a white solid. LCMS (ESI) m/z 304.1 [M+H]+; 1H NMR (400MHz, METHANOL-d4) 8.74 (s, 1H), 8.15 (s, 1H), 7.33 (s, 1H), 4.01 - 3.91 (m, 1H), 1.98 - 1.93 (m, 2H), 1.93 - 1.84 (m, 2H), 1.67 - 1.58 (m,2H), 1.01 (br d, J=13.6 Hz, 2H), 0.37 - 0.33 (m, 2H), 0.31 - 0.26 (m, 2H).
  • 12
  • [ 1211539-85-3 ]
  • [ 1955530-17-2 ]
  • [ 2637387-35-8 ]
YieldReaction ConditionsOperation in experiment
6.12% Stage #1: 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 30℃; for 0.5h; Stage #2: 2,2-difluorospiro[2.5]octan-6-amine hydrochloride In N,N-dimethyl-formamide at 30℃; for 1.5h; Inert atmosphere; 100 Example 100. MPL-164 Synthesis of 4-chloro-N-(1,1-difluorospiro[2.5]octan-6-yl)-1H-pyrrolo[2,3-c]pyridine-2- carboxamide To a solution of 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (50 mg, 254.34 umol, 1 eq) in DMF (1 mL) was added CDI (49.49 mg, 305.20 umol, 1.2 eq). The mixture was stirred at 30 °C for 0.5 hr. 2,2-difluorospiro[2.5]octan-6-amine (60.32 mg, 305.20 umol, 1.2 eq, HCl) was added. The mixture was stirred at 30 °C for 1.5 hr under N2. LC-MS showed reactant 1 was consumed completely and one main peak with desired mass was detected. The reaction mixture was added to H2O (10 mL) and stirred for 10 min, then extracted with EtOAc (30 mL x 3). The combined organic layers was dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. Compound 4-chloro-N-(2,2-difluorospiro[2.5]octan-6-yl)-1H- pyrrolo[2,3-c]pyridine- 2-carboxamide (5.3 mg, 15.57 umol, 6.12% yield, 99.833% purity) was obtained as a white solid. LCMS (ESI) m/z 340.1 [M+H]+; 1H NMR (400MHz, METHANOL-d4) = 8.72 (s, 1H), 8.13 (s, 1H), 7.31 (s, 1H), 4.05 - 3.94 (m, 1H), 2.03 (br d, J=9.0 Hz, 2H), 1.83 (br t, J=10.9 Hz, 2H), 1.69 - 1.45 (m, 4H), 1.17 - 1.08 (m, 2H).
  • 13
  • [ 1211539-85-3 ]
  • [ 1427380-18-4 ]
  • [ 2637387-36-9 ]
YieldReaction ConditionsOperation in experiment
12.6% With 1-methyl-1H-imidazole; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 12h; 101 Example 101. MPL-167 4-chloro-N- (4-fluoro-4-methyl-cyclohexyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide To a solution of 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (100 mg, 508.67 umol, 1 eq) in DMF (1 mL) was added 1-methylimidazole (208.82 mg, 2.54 mmol, 202.74 uL, 5 eq). [chloro(dimethylamino)methylene]-dimethyl-ammonium;hexafluorophosphate (214.08 mg, 763.01 umol, 1.5 eq) and 4-fluoro-4-methyl-cyclohexanamine (110.86 mg, 661.27 umol, 1.3 eq, HCl). The mixture was stirred at 25 °C for 12 h. LCMS showed there were no starting material and main desired compound. The reaction mixture was added to water (15 mL), then filtered and the filter cake was washed with 10 mL of water, dried in vacuo to give crude product. The crude product was purified by prep-HPLC(column: YMC-Actus Triart C18150*305u;mobile phase: [water(0.225%FA)-ACN];B%: 28%-55%,11min). The product 4-chloro-N- (4-fluoro-4-methyl- cyclohexyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (20 mg, 64.11 umol, 12.60% yield, 99.3% purity) was obtained as white soild. LCMS (ESI) m/z 310.1 [M+H]+; 1H NMR (500MHz, DMSO-d6) d = 12.61 (br s, 1H), 8.76 (s, 1H), 8.70 (d, J=8.2 Hz, 0.3H), 8.54 (d, J=7.6 Hz, 0.7H), 8.23 (s, 1H), 7.41 - 7.38 (m, 1H), 4.03 - 3.97 (m, 0.7H), 3.88 (br s, 0.3H), 1.89 - 1.83 (m, 3H), 1.77 - 1.63 (m, 3H), 1.63 - 1.54 (m, 2H), 1.42 (s, 1H), 1.38 (s, 1H), 1.35 (s, 0.5H), 1.30 (s, 0.5H).
  • 14
  • 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [ No CAS ]
  • [ 1193-43-7 ]
  • N-(4-bicyclo[2.2.2]octanyl)-4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.64% In N,N-dimethyl-formamide at 25℃; for 4h; Inert atmosphere; 103 Example 103. MPL-170 Synthesis of N-(4-bicyclo[2.2.2]octanyl)-4-chloro-1H-pyrrolo[2,3-c] pyridine-2-carboxamide To a solution of 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (50 mg, 254.34 umol, 1 eq) and bicyclo[2.2.2]octan-4-amine (61.68 mg, 381.50 umol, 1.5 eq, HCl) in DMF (1 mL) was added HOBt (51.55 mg, 381.50 umol, 1.5 eq) and EDCI (73.13 mg, 381.50 umol, 1.5 eq) TEA (77.21 mg, 763.01 umol, 106.20 uL, 3 eq), the mixture was stirred at 25 °C for 4 hr under N2. LC-MS showed the starting material 1 was consumed completely and one main peak with desired mass was detected. The mixture was added to water (15mL) and stirred for 10min, filtered and the filter cake was dried under reduced pressure. The product N-(4- bicyclo[2.2.2]octanyl)-4-chloro-1H-pyrrolo[2,3-c] pyridine-2-carboxamide (54.9 mg, 179.67 umol, 70.64% yield, 99.417% purity) was obtained as white solid. LCMS (ESI) m/z 304.0 [M+H] +; 1H NMR (500MHz, METHANOL-d4) = 12.34 (br s, 1H), 8.71 (s, 1H), 8.16 (s, 1H), 7.96 (s, 1H), 7.38 (s, 1H), 2.01 - 1.89 (m, 6H), 1.69 - 1.60 (m, 6H), 1.58 - 1.52 (m, 1H).
  • 15
  • [ 1330276-93-1 ]
  • [ 1211539-85-3 ]
  • [ 2637387-64-3 ]
YieldReaction ConditionsOperation in experiment
9.33% Stage #1: 4-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 30℃; for 0.5h; Stage #2: 6-silaspiro[5.5]undecan-3-amine In N,N-dimethyl-formamide at 30℃; for 11.5h; 132 Example 132. MPL-260 Synthesis of 4-chloro-N-(6-silaspiro[5.5]undecan-3-yl)-1H-pyrrolo[2,3-c]pyridine-2 - carboxamide To a solution of 4-chloro-1H-pyrrolo [2, 3-c] pyridine-2-carboxylic acid (50 mg, 254.34 umol, 1 eq) in DMF (1.5 mL) was added CDI (49.49 mg, 305.20 umol, 1.2 eq). The mixture was stirred at 30 °C for 0.5 h. Then 6-silaspiro[5.5]undecan-3-amine (55.96 mg, 305.20 umol, 1.2 eq) was added. The mixture was stirred at 30 °C for 11.5 h. TLC (Petroleum ether : EtOAc = 5 : 1, Rf = 0.5) showed there were no starting material and one major new spot with higher polarity was detected. The reaction was added dropwise to H2O (20 mL). The precipitation was collected by filter. The cake was transferred in bottom flask. The residue was purified by column chromatography (SiO2, Petroleum ether : EtOAc = 5 : 1). Compound 4-chloro-N-(6-silaspiro [5.5]undecan-3-yl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (8.6 mg, 23.73 umol, 9.33% yield, 99.880% purity) was obtained as a yellow solid (LCMS (ESI), m/z 362.0 [M+H] +). 1H NMR (500MHz, CHLOROFORM-d) d = 10.82 (br s, 1H), 8.85 (s, 1H), 8.29 (s, 1H), 6.93 (s, 1H), 6.29 (br d, J=7.3 Hz, 1H), 4.01 (br d, J=8.2 Hz, 1H),2.25 (br d, J=9.5 Hz, 2H), 1.76 - 1.64 (m, 6H), 1.43 (br s, 2H), 0.95 (br d, J=15.0 Hz, 2H), 0.79 - 0.69 (m, 4H), 0.68 - 0.62 (m, 2H).
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