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2-Aminocyclohexanol → 2-[3-(2-Methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridin-6-ylamino]-cyclohexanol

HRID 383286
Notes
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Reaction equation

HRID 383286 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([O:17][CH3:18])[CH:12]=3)=[CH:9][N:10]=2)[CH:7]=1.CC(C)([O-])C.[Na+].[NH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[OH:32]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C[C@@H](P(C1CCCCC1)C1CCCCC1)[C]1[C](P(C2C=CC=CC=2)C2C=CC=CC=2)[CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1.[Fe]>[CH3:18][O:17][C:13]1[CH:12]=[C:11]([C:8]2[N:6]3[CH:7]=[C:2]([NH:25][CH:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]4[OH:32])[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)[CH:16]=[CH:15][N:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 232862-AminocyclohexanolHCID 23676156Sodium t-butoxideHCID 684860916-Chloro-3-(2-methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridine2×

Product 1

HCID 252619052-[3-(2-Methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridin-6-ylamino]-cyclohexanol

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetate
Catalyst
HCID 178461697HCID 178461697, compoundCatalyst
HCID 80711,2-DimethoxyethaneSolvent

Procedure

6-Chloro-3-(2-methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridine (Intermediate G) (1 eq, 200 mg, 0.769 mmol), sodium tert-butoxide (2.4 eq, 1.8 mmol, 177 mg), palladium acetate (17 mg, 0.1 eq), (R)-1-[(1S)-2-(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine (43 mg, 0.1 eq) are stirred at RT under an inert atmosphere of argon in DME (3 ml) and degassed thoroughly before adding 2-aminocyclohexanol (2 eq, 1.53 mmol, 176 mg) The reaction is heated using microwave radiation at 100° C. for 2 hours. The majority of the solvent is removed in vacuo and the resulting residue is loaded onto a SCX-2 cartridge (resin loading 0.67 mmol/g) eluting with MeOH followed by 2M NH3 in MeOH. The methanolic ammonia fractions are concentrated in vacuo and further purified by flash chromatography (10% MeOH/EtOAc) to afford the title compound; [M+H]+=339

Workup

  1. customdegassed thoroughly
  2. temperatureis heated
  3. customat 100° C.
  4. customfor 2 hours
  5. customThe majority of the solvent is removed in vacuo
  6. washeluting with MeOH
  7. concentrationThe methanolic ammonia fractions are concentrated in vacuo
  8. customfurther purified by flash chromatography (10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-dbe25762c46e496a90e059e17300afc2
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367662B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes