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

HRID 383286
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HRID 383286 반응식
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
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참가 물질

7

반응물 3

HCID 232862-AminocyclohexanolHCID 23676156Sodium t-butoxideHCID 684860916-Chloro-3-(2-methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridine2회

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매
HCID 178461697
HCID 178461697, 화합물
촉매
HCID 80711,2-Dimethoxyethane용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-dbe25762c46e496a90e059e17300afc2
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08367662B2

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