Water → 5-([1,1'-biphenyl]-4-yl)-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-amine

HRID 929156ノート

反応式

HRID 929156 の反応式
C1CCN2C(=[N:5]CCC2)CC1.[C:12]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:17]=[CH:16][C:15]([C:18]2[N:23]=[C:22]3[N:24]=[C:25](S(C)(=O)=O)[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:21]3=[CH:20][C:19]=2[Cl:39])=[CH:14][CH:13]=1.C([O-])(=O)C.[NH4+].O>CN(C=O)C>[C:12]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:17]=[CH:16][C:15]([C:18]2[N:23]=[C:22]3[N:24]=[C:25]([NH2:5])[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:21]3=[CH:20][C:19]=2[Cl:39])=[CH:14][CH:13]=1

参加物

6

反応物 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 517165Ammonium AcetateHCID 682826082-[[6-Chloro-2-methylsulfonyl-5-(4-phenylphenyl)imidazo[4,5-b]pyridin-1-yl]methoxy]ethyl-trimethyl-silane

生成物 1

HCID 900418035-([1,1'-biphenyl]-4-yl)-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-amine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

DBU (0.204 ml, 1.354 mmol) was added to a stirred mixture of 5-([1,1′-biphenyl]-4-yl)-6-chloro-2-(methylsulfonyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridine (232 mg, 0.451 mmol) and ammonium acetate (348 mg, 4.51 mmol) in DMF (2 ml), and the mixture was stirred at room temperature overnight. Water (30 mL) was added and the mixture was extracted with ethyl acetate (2×30 mL). The combined organic fractions were washed with brine (saturated, 20 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.1% TFA. The combined fractions was concentrated, dissolved in MeOH, neutralized with NH4OH, concentrated, redissolved in MeOH, filtered through silica gel pad, washed with DCM:MeOH:NH4OH(10:1:0.1) and dried to give title compound. LC-MS: calculated for C24H27ClN4OSi 450.16 observed m/e: 451.13 (M+H)+ (Rt 1.25/2 min).

後処理

  1. extractionthe mixture was extracted with ethyl acetate (2×30 mL)
  2. washThe combined organic fractions were washed with brine (saturated, 20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by preparative HPLC Reverse phase (C-18)
  7. washeluting with acetonitrile/water+0.1% TFA
  8. concentrationThe combined fractions was concentrated
  9. dissolutiondissolved in MeOH
  10. concentrationconcentrated
  11. dissolutionredissolved in MeOH
  12. filtrationfiltered through silica gel pad
  13. washwashed with DCM:MeOH:NH4OH(10:1:0.1)
  14. customdried

出典と根拠

ORDレコード
ord-cbf3311dfbc341dbb8278dbf4627c064
出典データセット
uspto-grants-2016_03
特許番号
US09290517B2

反応ノート

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