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[ CAS No. 887341-00-6 ] {[proInfo.proName]}

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Chemical Structure| 887341-00-6
Chemical Structure| 887341-00-6
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Product Details of [ 887341-00-6 ]

CAS No. :887341-00-6 MDL No. :
Formula : C8H12N2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 152.19 Pubchem ID :-
Synonyms :

Safety of [ 887341-00-6 ]

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Application In Synthesis of [ 887341-00-6 ]

* 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 [ 887341-00-6 ]

[ 887341-00-6 ] Synthesis Path-Downstream   1~28

  • 1
  • [ 887341-00-6 ]
  • [ 4619-20-9 ]
  • C20H21NO2 [ No CAS ]
  • C20H21NO2 [ No CAS ]
Reference： [1]Synlett,2008,p. 1687 - 1689
  • 2
  • [ 28466-21-9 ]
  • [ 887341-00-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258557-41-3 ]
YieldReaction ConditionsOperation in experiment
Example 127 (1S,2S,3R,4R)-3-({5-chloro-2-[(1,3,5-trimethyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[28466-21-9]1,3,5-trimethyl-1H-pyrazol-4-amine</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4,5-trichloropyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-d6) ppm 1.36 (d, J=8.48 Hz, 1H) 1.95 (s, 3H) 1.99-2.14 (m, 3H) 2.43 (d, J=8.14 Hz, 1H) 2.61 (s, 1H) 2.82 (s, 1H) 3.52-3.71 (m, 3H) 3.95 (s, 1H) 6.11 (br s, 1H) 6.28 (dd, J=5.43, 2.71 Hz, 1H) 7.19 (s, 1H) 7.34 (d, J=7.80 Hz, 1H) 7.68 (s, 1H) 7.76 (s, 1H) 7.95 (s, 1H); MS (ESI(+)) m/e 388 (M+H)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 3
  • [ 28466-21-9 ]
  • [ 887341-00-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258557-44-6 ]
YieldReaction ConditionsOperation in experiment
Example 128 (1S,2S,3R,4R)-3-({5-bromo-2-[(1,3,5-trimethyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[28466-21-9]1,3,5-trimethyl-1H-pyrazol-4-amine</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4-dichloro-5-bromopyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-d6) ppm 1.35 (d, J=8.82 Hz, 1H) 1.95 (s, 3H) 1.99-2.12 (m, 4H) 2.42 (d, J=8.82 Hz, 1H) 2.54-2.63 (m, 1H) 2.81 (s, 1H) 3.62 (s, 3H) 6.07 (br s, 1H) 6.27 (dd, J=5.59, 2.88 Hz, 1H) 7.18 (s, 1H) 7.29 (d, J=7.80 Hz, 1H) 7.67 (s, 1H) 7.83 (s, 1H) 7.96 (s, 1H); MS (ESI(+)) m/e 432, 434 (M+H)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 4
  • [ 876343-24-7 ]
  • [ 887341-00-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258555-96-2 ]
YieldReaction ConditionsOperation in experiment
Example 62 (1S,2S,3R,4R)-3-[2-[(1-ethyl-1H-pyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino}bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[876343-24-7]1-ethyl-1H-pyrazol-4-amine</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4-dichloro-5-(trifluoromethyl)pyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-D6) ppm 1.28-1.47 (m, 4H) 2.03 (d, J=8.82 Hz, 1H) 2.86 (d, J=13.2 Hz, 2H) 4.08 (q, J=7.1 Hz, 2H) 4.17 (t, J=6.8 Hz, 1H) 6.28 (dd, J=5.6, 2.88 Hz, 1H) 6.38 (s, 1H) 7.30 (s, 1H) 7.59 (s, 1H) 7.77 (d, J=22.4 Hz, 3H) 8.11 (s, 2H) 9.20-9.66 (m, 1H); MS (ESI(+)) m/e 408 (M+1)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 5
  • [ 876343-24-7 ]
  • [ 887341-00-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258556-12-5 ]
YieldReaction ConditionsOperation in experiment
Example 42 (1S,2S,3R,4R)-3-({5-chloro-2-[(1-ethyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[876343-24-7]1-ethyl-1H-pyrazol-4-amine</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4,5-trichloropyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (501 MHz, DMSO-D6, T=90° C.) ppm 1.36 (t, J=7.2 Hz, 3H) 1.42 (d, J=8.8 Hz, 1H) 2.12 (d, J=8.8 Hz, 1H) 2.55 (d, J=8.3 Hz, 1H) 2.79 (s, 1H) 2.88 (s, 1H) 4.05 (q, J=7.2 Hz, 2H) 4.15 (t, J=7.8 Hz, 1H) 6.23-6.38 (m, 2H) 6.81-7.02 (m, 1H) 7.50 (s, 1H) 7.52 (d, J=7.4 Hz, 1H) 7.71 (s, 1H) 7.84 (s, 1H) 8.70 (s, 1H); MS (ESI(+)) m/e 374 (M+H)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 6
  • [ 876343-24-7 ]
  • [ 887341-00-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258556-14-7 ]
YieldReaction ConditionsOperation in experiment
Example 79 (1S,2S,3R,4R)-3-({5-bromo-2-[(1-ethyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[876343-24-7]1-ethyl-1H-pyrazol-4-amine</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4-dichloro-5-bromopyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (400 MHz, DMSO-D6, T=90° C.) ppm 1.36 (t, J=7.32 Hz, 3H) 1.42 (d, J=8.54 Hz, 1H) 2.12 (d, J=8.85 Hz, 1H) 2.55 (d, J=7.93 Hz, 1H) 2.77 (s, 1H) 2.88 (s, 1H) 4.05 (q, J=7.32 Hz, 2H) 4.16 (t, J=7.93 Hz, 1H) 6.21-6.39 (m, 2H) 6.77-6.97 (m, 1H) 7.36-7.54 (m, 3H) 7.70 (s, 1H) 7.91 (s, 1H) 8.68 (s, 1H); MS (ESI(+)) m/e 420 (M+H)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 7
  • [ 876343-24-7 ]
  • [ 887341-00-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258557-63-9 ]
YieldReaction ConditionsOperation in experiment
Example 140 (1S,2S,3R,4R)-3-({2-[(1-ethyl-1H-pyrazol-4-yl)amino]-5-nitropyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[876343-24-7]1-ethyl-1H-pyrazol-4-amine</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4-dichloro-5-nitropyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (400 MHz, DMSO-d6) ppm 1.38 (t, J=7.32 Hz, 3H) 1.42-1.50 (m, 1H) 2.19 (d, J=8.85 Hz, 1H) 2.58 (d, J=7.93 Hz, 1H) 2.84 (s, 1H) 2.91 (s, 1H) 4.10 (q, J=7.32 Hz, 2H) 4.38 (s, 1H) 6.29 (dd, J=5.49, 3.05 Hz, 1H) 6.37 (dd, J=5.65, 2.90 Hz, 1H) 6.80 (br s, 1H) 7.31 (br s, 1H) 7.63 (s, 1H) 7.79 (s, 1H) 8.89 (s, 1H) 9.68 (br s, 1H) 9.98 (br s, 1H); MS (ESI(+)) m/e 385 (M+H)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 8
  • [ 97421-16-4 ]
  • [ 887341-00-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258557-07-1 ]
YieldReaction ConditionsOperation in experiment
Example 98B (1S,2S,3R,4R)-3-({5-chloro-2-[(1-isopropyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[97421-16-4]1-isopropyl-1H-pyrazol-4-amine</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4,5-trichloropyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-D6) ppm 1.39 (d, J=6.74 Hz, 7H) 2.12 (d, J=8.33 Hz, 1H) 2.88 (s, 1H) 4.14 (t, J=7.54 Hz, 1H) 4.34-4.49 (m, 1H) 6.27 (d, J=3.17 Hz, 1H) 6.37 (d, J=5.16 Hz, 1H) 7.25 (s, 1H) 7.51 (s, 1H) 7.65 (s, 1H) 7.76 (d, J=5.95 Hz, 3H) 7.89 (s, 1H) 9.08 (s, 1H); MS (ESI(+)) m/e 388 (M+H)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 9
  • [ 97421-16-4 ]
  • [ 887341-00-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258557-21-9 ]
YieldReaction ConditionsOperation in experiment
Example 112 (1S,2S,3R,4R)-3-({5-bromo-2-[(1-isopropyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[97421-16-4]1-isopropyl-1H-pyrazol-4-amine</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4-dichloro-5-bromopyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-d6) ppm 1.39 (d, J=6.78 Hz, 6H) 2.12 (d, J=8.82 Hz, 1H) 2.75 (s, 1H) 2.75 (s, 1H) 2.87 (s, 1H) 2.87 (s, 1H) 4.15 (t, J=7.97 Hz, 1H) 4.31-4.49 (m, 1H) 6.28 (s, 1H) 6.38 (s, 1H) 7.23 (s, 1H) 7.51 (s, 1H) 7.58 (s, 1H) 7.74 (s, 2H) 7.95 (s, 1H) 9.07 (s, 1H); MS (ESI(+)) m/e 432 (M+H)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 10
  • [ 919278-39-0 ]
  • [ 887341-00-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258556-16-9 ]
YieldReaction ConditionsOperation in experiment
Example 64 (1S,2S,3R,4R)-3-[2-[1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]amino}-5-(trifluoromethyl)pyrimidin-4-yl]amino}bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[919278-39-0]1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-amine</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4-dichloro-5-(trifluoromethyl)pyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (501 MHz, DMSO-D6) ppm 1.28 (d, J=5.7 Hz, 2H) 1.41 (d, J=8.5 Hz, 1H) 2.05 (d, J=9.0 Hz, 1H) 2.53 (d, J=8.3 Hz, 1H) 2.84 (d, J=35.1 Hz, 2H) 4.20 (t, J=7.5 Hz, 1H) 4.88-5.07 (m, 2H) 6.23-6.35 (m, 2H) 7.74 (s, 1H) 7.88 (d, J=19.7 Hz, 2H) 8.11 (s, 1H) 9.28 (s, 1H); MS (ESI(+)) m/e 462 (M+1)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 11
  • [ 919278-39-0 ]
  • [ 887341-00-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258556-75-0 ]
YieldReaction ConditionsOperation in experiment
Example 66 (1S,2S,3R,4R)-3-[(5-chloro-2-[1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]amino}pyrimidin-4-yl)amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[919278-39-0]1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-amine</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4,5-trichloropyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-D6) ppm 1.41 (d, J=8.7 Hz, 1H) 2.10 (d, J=8.7 Hz, 1H) 2.82 (d, J=31.7 Hz, 2H) 4.11 (t, J=7.5 Hz, 1H) 5.06 (q, J=9.4 Hz, 2H) 6.13-6.44 (m, 2H) 7.26 (s, 1H) 7.55-7.95 (m, 6H) 9.20 (s, 1H); MS (ESI(+)) m/e 428 (M+1)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 12
  • [ 948570-74-9 ]
  • [ 887341-00-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258557-05-9 ]
YieldReaction ConditionsOperation in experiment
Example 96B (1S,2S,3R,4R)-3-[(5-chloro-2-[1-(2-methoxyethyl)-1H-pyrazol-4-yl]amino}pyrimidin-4-yl)amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[948570-74-9]1-(2-methoxyethyl)-1H-pyrazol-4-amine</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4,5-trichloropyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-d6) ppm 1.41 (d, J=9.12 Hz, 1H) 2.10 (d, J=8.72 Hz, 1H) 2.55 (s, 1H) 2.78 (s, 1H) 2.88 (s, 1H) 3.21 (s, 3H) 3.64 (t, J=5.16 Hz, 2H) 4.11 (t, J=7.73 Hz, 1H) 4.17 (t, J=5.35 Hz, 2H) 6.34 (d, J=8.33 Hz, 2H) 7.26 (s, 1H) 7.51 (s, 1H) 7.70-7.83 (m, 3H) 7.89 (s, 1H) 9.11 (s, 1H); MS (ESI(+)) m/e 404 (M+H)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 13
  • [ 948570-74-9 ]
  • [ 887341-00-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258557-15-1 ]
YieldReaction ConditionsOperation in experiment
Example 106 (1S,2S,3R,4R)-3-[(5-bromo-2-[1-(2-methoxyethyl)-1H-pyrazol-4-yl]amino}pyrimidin-4-yl)amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[948570-74-9]1-(2-methoxyethyl)-1H-pyrazol-4-amine</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4-dichloro-5-bromopyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-d6) ppm 1.41 (d, J=8.81 Hz, 1H) 2.10 (d, J=9.15 Hz, 1H) 2.77 (s, 1H) 2.87 (s, 1H) 3.22 (s, 3H) 3.64 (t, J=5.26 Hz, 2H) 4.11 (t, J=7.80 Hz, 1H) 4.17 (t, J=5.26 Hz, 2H) 6.31-6.38 (m, 2H) 7.25 (s, 1H) 7.52 (s, 1H) 7.76 (d, J=12.54 Hz, 3H) 7.95 (s, 1H) 9.12 (s, 1H); MS (ESI(+)) m/e 449 (M+H)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 14
  • [ 948571-47-9 ]
  • [ 887341-00-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258556-10-3 ]
YieldReaction ConditionsOperation in experiment
Example 63 (1S,2S,3R,4R)-3-[2-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]amino}-5-(trifluoromethyl)pyrimidin-4-yl]amino}bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[948571-47-9]2-(4-amino-1H-pyrazol-1-yl)ethanol</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4-dichloro-5-(trifluoromethyl)pyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-D6) ppm 1.14-1.31 (m, 1H) 1.41 (d, J=8.8 Hz, 1H) 2.03 (d, J=8.8 Hz, 1H) 2.88 (s, 2H) 3.71 (q, J=5.4 Hz, 2H) 4.00-4.13 (m, 2H) 4.17 (t, J=7.1 Hz, 1H) 4.88 (t, J=4.9 Hz, 1H) 6.37 (s, 2H) 7.30 (s, 1H) 7.61 (s, 1H) 7.78 (d, J=18.7 Hz, 3H) 8.04-8.18 (m, 1H) 9.27-9.66 (m, 1H); MS (ESI(+)) m/e 424 (M+1)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 15
  • [ 948571-47-9 ]
  • [ 887341-00-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258556-74-9 ]
YieldReaction ConditionsOperation in experiment
Example 65 (1S,2S,3R,4R)-3-[(5-chloro-2-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]amino}pyrimidin-4-yl)amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[948571-47-9]2-(4-amino-1H-pyrazol-1-yl)ethanol</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4,5-trichloropyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-D6) ppm 1.41 (d, J=8.7 Hz, 1H) 2.10 (d, J=8.7 Hz, 1H) 2.78 (s, 1H) 2.88 (s, 1H) 3.17 (d, J=5.2 Hz, 1H) 3.70 (q, J=5.6 Hz, 2H) 3.99-4.13 (m, 3H) 4.87 (t, J=5.4 Hz, 1H) 6.35 (s, 2H) 7.26 (s, 1H) 7.52 (s, 1H) 7.77 (s, 3H) 7.89 (s, 1H) 9.11 (s, 1H); MS (ESI(+)) m/e 390 (M+1)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 16
  • [ 887341-00-6 ]
  • [ 121983-36-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258557-96-8 ]
YieldReaction ConditionsOperation in experiment
170 (1S,2S,3R,4R)-3-({5-bromo-2-[(1,5-dimethyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide Example 170 (1S,2S,3R,4R)-3-({5-bromo-2-[(1,5-dimethyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting 1,5-dimethyl-1H-pyrazol-4-amine for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4-dichloro-5-bromopyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (400 MHz, DMSO-d6) ppm 1.38 (d, J=8.85 Hz, 1H) 2.08 (d, J=8.85 Hz, 1H) 2.15 (s, 3H) 2.70 (s, 1H) 2.85 (s, 1H) 3.68 (s, 3H) 3.71 (q, J=5.19 Hz, 1H) 3.96-4.13 (m, 1H) 6.16 (dd, J=5.49, 3.05 Hz, 1H) 6.27 (dd, J=5.65, 2.90 Hz, 1H) 6.82 (s, 1H) 7.22-7.42 (m, J=7.63 Hz, 2H) 7.47 (s, 1H) 7.85 (s, 1H) 7.91 (s, 1H); MS (ESI(+)) m/e 418, 420 (M+H)+.
Reference： [1]Current Patent Assignee: ABBVIE INC - US2010/317680, 2010, A1
  • 17
  • [ 887341-00-6 ]
  • [ 121983-36-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258558-46-1 ]
YieldReaction ConditionsOperation in experiment
169 (1S,2S,3R,4R)-3-({5-chloro-2-[(1,5-dimethyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide Example 169 (1S,2S,3R,4R)-3-({5-chloro-2-[(1,5-dimethyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting 1,5-dimethyl-1H-pyrazol-4-amine for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4,5-trichloropyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (400 MHz, DMSO-d6, T=90° C.) ppm 1.38 (d, J=8.85 Hz, 1H) 2.08 (d, J=8.85 Hz, 1H) 2.15 (s, 3H) 2.71 (s, 1H) 2.85 (s, 1H) 3.65-3.71 (m, 3H) 3.97-4.10 (m, 1H) 6.17 (dd, J=5.49, 3.05 Hz, 1H) 6.28 (dd, J=5.65, 2.90 Hz, 1H) 6.84 (br s, 1H) 7.39 (d, J=7.93 Hz, 1H) 7.47 (s, 1H) 7.78 (s, 1H) 7.89 (s, 1H); MS (ESI(+)) m/e 374 (M+H)+.
Reference： [1]Current Patent Assignee: ABBVIE INC - US2010/317680, 2010, A1
  • 18
  • [ 64517-88-0 ]
  • [ 887341-00-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258557-55-9 ]
YieldReaction ConditionsOperation in experiment
Example 134 (1S,2S,3R,4R)-3-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[64517-88-0]1,3-dimethyl-1H-pyrazol-4-amine</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4,5-trichloropyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (400 MHz, DMSO-d6, T=90 C.) ppm 1.34-1.47 (m, 1H) 2.06-2.16 (m, 4H) 2.73 (s, 1H) 2.87 (s, 1H) 3.71 (s, 3H) 4.03-4.15 (m, 1H) 6.21 (dd, J=5.49, 3.05 Hz, 1H) 6.31 (dd, J=5.65, 2.90 Hz, 1H) 7.42 (d, J=7.63 Hz, 1H) 7.65 (s, 1H) 7.81 (s, 1H) 7.87 (s, 1H); MS (ESI(+)) m/e 374 (M+H)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 19
  • [ 64517-88-0 ]
  • [ 887341-00-6 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258557-56-0 ]
YieldReaction ConditionsOperation in experiment
Example 135 (1S,2S,3R,4R)-3-({5-bromo-2-[(1,3-dimethyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[64517-88-0]1,3-dimethyl-1H-pyrazol-4-amine</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4-dichloro-5-bromopyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (400 MHz, DMSO-d6) ppm 1.37-1.43 (m, 1H) 2.05-2.17 (m, 4H) 2.49-2.53 (m, 1H) 2.72 (s, 1H) 2.86 (s, 1H) 3.70 (s, 3H) 4.03-4.14 (m, 1H) 6.20 (dd, J=5.80, 3.05 Hz, 1H) 6.30 (dd, J=5.65, 2.90 Hz, 1H) 7.38 (d, J=7.93 Hz, 1H) 7.64 (s, 1H) 7.88 (s, 1H) 7.91 (s, 1H); MS (ESI(+)) m/e 418, 420 (M+H)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 20
  • [ 887341-00-6 ]
  • [ 28466-62-8 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258557-69-5 ]
YieldReaction ConditionsOperation in experiment
Example 144B (1S,2S,3R,4R)-3-({2-[(1-benzyl-1H-pyrazol-4-yl)amino]-5-chloropyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[28466-62-8]1-benzyl-1H-pyrazol-4-amine</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4,5-trichloropyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-d6) ppm 1.38 (d, J=8.72 Hz, 1H) 2.08 (d, J=8.72 Hz, 1H) 2.73 (s, 1H) 2.86 (s, 1H) 4.02-4.10 (m, 1H) 5.27 (s, 2H) 6.13 (s, 1H) 6.31 (dd, J=5.55, 2.78 Hz, 1H) 7.19 (d, J=7.93 Hz, 2H) 7.23-7.39 (m, 4H) 7.56 (s, 1H) 7.78 (s, 3H) 7.88 (s, 1H) 9.14 (s, 1H); MS (ESI(+)) m/e 436 (M+H)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 21
  • [ 887341-00-6 ]
  • [ 28466-62-8 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258557-75-3 ]
YieldReaction ConditionsOperation in experiment
Example 149 (1S,2S,3R,4R)-3-({2-[(1-benzyl-1H-pyrazol-4-yl)amino]-5-bromopyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting <strong>[28466-62-8]1-benzyl-1H-pyrazol-4-amine</strong> for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4-dichloro-5-bromopyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-d6) ppm 1.38 (d, J=8.82 Hz, 1H) 2.08 (d, J=8.82 Hz, 1H) 2.72 (s, 1H) 2.85 (s, 1H) 3.97-4.13 (m, 1H) 5.27 (s, 3H) 6.12 (s, 1H) 6.30 (d, J=8.48 Hz, 1H) 7.15-7.23 (m, 2H) 7.25-7.37 (m, 4H) 7.56 (s, 1H) 7.67 (s, 1H) 7.77 (d, J=7.46 Hz, 2H) 7.94 (s, 1H) 9.14 (s, 1H); MS (ESI(+)) m/e 480 (M+H)+.
Reference： [1]Patent: US2010/317680,2010,A1
  • 22
  • [ 887341-00-6 ]
  • [ 1006348-46-4 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • isopropyl{4-[(4-[(1R,2R,3S,4S)-3-(aminocarbonyl)bicyclo[2.2.1]hept-5-ene-2-yl]amino}-5-chloropyrimidin-2-yl)amino]-1H-pyrazol-1-yl}acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
78 isopropyl{4-[(4-[(1R,2R,3S,4S)-3-(aminocarbonyl)bicyclo[2.2.1]hept-5-ene-2-yl]amino}-5-chloropyrimidin-2-yl)amino]-1H-pyrazol-1-yl}acetate Example 78 isopropyl{4-[(4-[(1R,2R,3S,4S)-3-(aminocarbonyl)bicyclo[2.2.1]hept-5-ene-2-yl]amino}-5-chloropyrimidin-2-yl)amino]-1H-pyrazol-1-yl}acetate The title compound was prepared as described in Example 1, substituting 2-(4-amino-1H-pyrazol-1-yl)acetic acid for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4,5-trichloropyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (400 MHz, DMSO-D6, T=90° C.) ppm 1.14-1.25 (m, 7H) 1.42 (d, 1H) 2.11 (d, J=9.2 Hz, 1H) 2.54 (d, J=8.6 Hz, 1H) 2.79 (s, 1H) 2.88 (s, 1H) 4.13 (t, J=8.1 Hz, 1H) 4.87 (s, 2H) 4.90-5.07 (m, 1H) 6.21-6.36 (m, 2H) 7.51-7.62 (m, 2H) 7.77 (s, 1H) 7.85 (s, 1H) 8.76 (s, 1H); MS (ESI(+)) m/e 446.0 (M+H)+.
Reference： [1]Current Patent Assignee: ABBVIE INC - US2010/317680, 2010, A1
  • 23
  • [ 887341-00-6 ]
  • [ 1006348-46-4 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258557-12-8 ]
YieldReaction ConditionsOperation in experiment
In <i>tert</i>-butyl alcohol 103 {4-[(4-[(1R,2R,3S,4S)-3-carbamoylbicyclo[2.2.1]hept-5-ene-2-yl]amino}-5-chloropyrimidin-2-yl)amino]-1H-pyrazol-1-yl}acetic acid Example 103 {4-[(4-[(1R,2R,3S,4S)-3-carbamoylbicyclo[2.2.1]hept-5-ene-2-yl]amino}-5-chloropyrimidin-2-yl)amino]-1H-pyrazol-1-yl}acetic acid The title compound was prepared as described in Example 1, substituting 2-(4-amino-1H-pyrazol-1-yl)acetic acid for 1-methyl-1H-pyrazol-4-amine and tert-butanol for 2-propanol in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4,5-trichloropyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (400 MHz, DMSO-d6; T=90° C.) ppm 1.42 (d, J=8.85 Hz, 1H) 2.06 (d, J=9.16 Hz, 1H) 2.56 (d, J=7.93 Hz, 1H) 2.84 (s, 1H) 2.91 (s, 1H) 4.10 (t, J=7.32 Hz, 1H) 4.85 (s, 2H) 6.25 (dd, J=5.49, 3.05 Hz, 1H) 6.33 (dd, J=5.65, 2.90 Hz, 1H) 7.00 (br s, 1H) 7.45-7.66 (m, 2H) 7.80 (s, 1H) 7.96 (s, 1H) 8.52 (br s, 1H) 9.38 (br s, 1H); MS (ESI(+)) m/e 404 (M+H)+.
Reference： [1]Current Patent Assignee: ABBVIE INC - US2010/317680, 2010, A1
  • 24
  • [ 887341-00-6 ]
  • [ 1201363-83-8 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258556-42-1 ]
YieldReaction ConditionsOperation in experiment
91 (1S,2S,3R,4R)-3-[5-chloro-2-({1-[2-(4-methylpiperazin-1-yl)ethyl]-1H-pyrazol-4-yl}amino)pyrimidin-4-yl]amino}bicyclo[2.2.1]hept-5-ene-2-carboxamide Example 91 (1S,2S,3R,4R)-3-[5-chloro-2-({1-[2-(4-methylpiperazin-1-yl)ethyl]-1H-pyrazol-4-yl}amino)pyrimidin-4-yl]amino}bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting 1-(2-(4-methylpiperazin-1-yl)ethyl)-1H-pyrazol-4-amine for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4,5-trichloropyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-d6) d ppm 1.41 (d, J=8.48 Hz, 1H) 2.06-2.13 (m, 1H) 2.12 (s, 3H) 2.20-2.33 (br m, 4H) 2.34-2.43 (br m, 4H) 2.51-2.58 (m, 1H) 2.66 (t, J=6.78 Hz, 2H) 2.78 (s, 1H) 2.88 (s, 1H) 4.07-4.16 (m, 3H) 6.27-6.39 (m, 2H) 7.25 (s, 1H) 7.51 (s, 1H) 7.70-7.82 (m, J=8.65, 8.65 Hz, 3H) 7.88 (s, 1H) 9.09 (s, 1H); MS (ESI(+)) m/e 472 (M+H)+.
Reference： [1]Current Patent Assignee: ABBVIE INC - US2010/317680, 2010, A1
  • 25
  • [ 887341-00-6 ]
  • [ 1201363-83-8 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258557-03-7 ]
YieldReaction ConditionsOperation in experiment
94 (1S,2S,3R,4R)-3-[5-bromo-2-({1-[2-(4-methylpiperazin-1-yl)ethyl]-1H-pyrazol-4-yl}amino)pyrimidin-4-yl]amino}bicyclo[2.2.1]hept-5-ene-2-carboxamide Example 94 (1S,2S,3R,4R)-3-[5-bromo-2-({1-[2-(4-methylpiperazin-1-yl)ethyl]-1H-pyrazol-4-yl}amino)pyrimidin-4-yl]amino}bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting 1-(2-(4-methylpiperazin-1-yl)ethyl)-1H-pyrazol-4-amine for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4-dichloro-5-bromopyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-d6) δppm 1.41 (d, J=8.81 Hz, 1H) 2.10 (d, J=8.81 Hz, 1H) 2.18 (s, 3H) 2.28-2.47 (m, 8H) 2.52-2.56 (m, 1H) 2.67 (t, J=6.78 Hz, 2H) 2.77 (s, 1H) 2.88 (s, 1H) 4.08-4.16 (m, 3H) 6.25-6.41 (m, 2H) 7.25 (s, 1H) 7.51 (s, 1H) 7.67-7.83 (m, 3H) 7.95 (s, 1H) 9.11 (s, 1H); MS (ESI(+)) m/e 516, 518, Br pattern, (M+H)+.
Reference： [1]Current Patent Assignee: ABBVIE INC - US2010/317680, 2010, A1
  • 26
  • [ 887341-00-6 ]
  • [ 1190380-64-3 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258557-28-6 ]
YieldReaction ConditionsOperation in experiment
118.B (1S,2S,3R,4R)-3-({5-chloro-2-[(1-cyclobutyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide Example 118B (1S,2S,3R,4R)-3-({5-chloro-2-[(1-cyclobutyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting 1-cyclobutyl-1H-pyrazol-4-yl-amine for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4,5-trichloropyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-d6) ppm 1.42 (d, J=8.82 Hz, 1H) 1.71-1.83 (m, 2H) 2.11 (d, J=8.82 Hz, 1H) 2.29-2.46 (m, 4H) 2.77 (s, 1H) 2.88 (s, 1H) 4.14 (t, J=7.97 Hz, 1H) 4.65-4.81 (m, 1H) 6.28 (d, J=8.48 Hz, 1H) 6.38 (d, J=8.14 Hz, 1H) 7.24 (s, 1H) 7.53 (s, 1H) 7.68 (s, 1H) 7.79 (s, 2H) 7.89 (s, 1H) 9.09 (s, 1H); MS (ESI(+)) m/e 400 (M+H)+.
Reference： [1]Current Patent Assignee: ABBVIE INC - US2010/317680, 2010, A1
  • 27
  • [ 887341-00-6 ]
  • [ 1190380-64-3 ]
  • (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide [ No CAS ]
  • [ 1258557-35-5 ]
YieldReaction ConditionsOperation in experiment
123 (1S,2S,3R,4R)-3-({5-bromo-2-[(1-cyclobutyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide Example 123 (1S,2S,3R,4R)-3-({5-bromo-2-[(1-cyclobutyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}amino)bicyclo[2.2.1]hept-5-ene-2-carboxamide The title compound was prepared as described in Example 1, substituting 1-cyclobutyl-1H-pyrazol-4-yl-amine for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide for (+/-)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4-dichloro-5-bromopyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-d6) ppm 1.41 (d, J=8.82 Hz, 1H) 1.69-1.83 (m, 2H) 2.11 (d, J=8.82 Hz, 2H) 2.30-2.43 (m, 4H) 2.76 (s, 1H) 2.88 (s, 1H) 4.14 (t, J=7.46 Hz, 1H) 4.62-4.80 (m, 1H) 6.28 (d, J=5.76 Hz, 1H) 6.37 (d, J=5.09 Hz, 1H) 7.23 (s, 1H) 7.54 (s, 1H) 7.63 (s, 1H) 7.77 (s, 2H) 7.95 (s, 1H) 9.10 (s, 1H); MS (ESI(+)) m/e 445 (M+H)+.
Reference： [1]Current Patent Assignee: ABBVIE INC - US2010/317680, 2010, A1
  • 28
  • [ 887341-00-6 ]
  • [ 1137278-39-7 ]
  • C13H12ClN5OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Sodium hydrogenocarbonate In lithium hydroxide monohydrate; isopropanol at 60 - 100℃; General procedures A: General procedure: an i-PrOH/H2O (9:1, 0.25 - 0.5 M) solution of amine (S-1), 5,6- or 6,6-fused-2,4-dichloropyrimidine (1.0 - 1.2 eq.) and NaHCO3 (2.5 - 3.0 eq.) was stirred at 60 - 100 °C. Reaction was monitored by LC-MS, and was stopped when S-1 left. Solvent was removed in vacuo and product was purified by silica gel chromatography.
With Sodium hydrogenocarbonate In lithium hydroxide monohydrate; isopropanol at 60 - 100℃; General procedures A: General procedure: an i-PrOH/H2O (9:1, 0.25 - 0.5 M) solution of amine (S-1), 5,6- or 6,6-fused-2,4-dichloropyrimidine (1.0 - 1.2 eq.) and NaHCO3 (2.5 - 3.0 eq.) was stirred at 60 - 100 °C. Reaction was monitored by LC-MS, and was stopped when S-1 left. Solvent was removed in vacuo and product was purified by silica gel chromatography.
Reference： [1]Chen, Yan; Tso, Kin; Heckrodt, Thilo J.; Li, Hui; Yen, Rose; Lin, Nan; Singh, Rajinder; Taylor, Vanessa; Masuda, Esteban S.; Park, Gary; Payan, Donald G. [Bioorganic and Medicinal Chemistry Letters, 2022, vol. 73]
[2]Chen, Yan; Tso, Kin; Heckrodt, Thilo J.; Li, Hui; Yen, Rose; Lin, Nan; Singh, Rajinder; Taylor, Vanessa; Masuda, Esteban S.; Park, Gary; Payan, Donald G. [Bioorganic and Medicinal Chemistry Letters, 2022, vol. 73]

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