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Potassium Iodide → N-(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)-1-(4-methoxybenzyl)-3-methyl-1H-indazol-5-amine

HRID 1039094
Notes
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Reaction equation

HRID 1039094 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=3)[C:10]([CH3:18])=[N:9]2)=[CH:5][CH:4]=1.CC1C=CC(S(O[CH2:32][CH2:33][C@@H:34]2[CH2:36][C@@H:35]2[CH:37]2[CH2:42][CH2:41][N:40]([C:43]3[N:48]=[CH:47][C:46]([Cl:49])=[CH:45][N:44]=3)[CH2:39][CH2:38]2)(=O)=O)=CC=1.[I-].[K+]>C(#N)C.O>[Cl:49][C:46]1[CH:45]=[N:44][C:43]([N:40]2[CH2:41][CH2:42][CH:37]([C@H:35]3[CH2:36][C@H:34]3[CH2:33][CH2:32][NH:17][C:13]3[CH:12]=[C:11]4[C:16](=[CH:15][CH:14]=3)[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:20][CH:19]=3)[N:9]=[C:10]4[CH3:18])[CH2:38][CH2:39]2)=[N:48][CH:47]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 669270631-(4-methoxybenzyl)-3-methyl-1H-indazol-5-amineHCID 866661412-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl 4-methylbenzenesulfonate

Product 1

HCID 67778018N-(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)-1-(4-methoxybenzyl)-3-methyl-1H-indazol-5-amine

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

1-(4-methoxybenzyl)-3-methyl-1H-indazol-5-amine (51 mg, 0.34 mmol) from step 2 of this example, 2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl 4-methylbenzenesulfonate from step 1 of Example 5 (75 mg, 0.17 mmol) and potassium iodide (3 mg, 0.017 mmol) combined and the solids slurried in acetonitrile. The slurry was reacted in the microwave with stirring for 80 minutes at 110° C. using normal power. The mixture was cooled to RT, diluted with 4:1 water:saturated sodium bicarbonate (40 ml), extracted with EtOAc (3×40 ml), the organic fractions combined, washed with brine, dried over Na2SO4, filtered and the volatiles removed in vacuum. The product was purified by chromatography on SiO2 eluting with 10% acetone:DCM to give the titled compound.

Workup

  1. customThe slurry was reacted in the microwave
  2. temperatureThe mixture was cooled to RT
  3. extractionsaturated sodium bicarbonate (40 ml), extracted with EtOAc (3×40 ml)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe volatiles removed in vacuum
  8. customThe product was purified by chromatography on SiO2 eluting with 10% acetone

Sources & evidence

ORD record
ord-781ad068dea24ff4a1e3c261ea99c3c4
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08552022B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes