Hydrochloric Acid → 8-(cyclohexylmethoxy)-2-methyl-N-{(1S)-3-[(methylsulfonyl)amino]-3-oxo-1-phenylpropyl}imidazolo[1,2-a]pyridine-3-carboxamide

HRID 64489ノート

反応式

HRID 64489 の反応式
[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][C@H:22]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:23][C:24]([OH:26])=O)=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:45][S:46]([NH2:49])(=[O:48])=[O:47].C1CCN2C(=NCCC2)CC1.Cl>CN(C=O)C.C(OCC)(=O)C>[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][C@H:22]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:23][C:24]([NH:49][S:46]([CH3:45])(=[O:48])=[O:47])=[O:26])=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 71478528HCID 71478528、化合物

生成物 1

HCID 867135228-(cyclohexylmethoxy)-2-methyl-N-{(1S)-3-[(methylsulfonyl)amino]-3-oxo-1-phenylpropyl}imidazolo[1,2-a]pyridine-3-carboxamide収率 34.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 100 mg of (3S)-3-({[8-(cyclohexylmethoxy)-2-methylimidazolo[1,2-a]pyridin-3-yl]carbonyl}amino)-3-phenylpropanoic acid in 1 mL of DMF was added 43 mg of 1,1′-carbonyldiimidazole, followed by stirring for 30 minutes. To the reaction solution were added 24 mg of methanesulfonamide and 0.039 mL of 1,8-diazabicyclo[5.4.0]-7-undecene, followed by stirring for 5 hours. To the reaction mixture were added 1 M hydrochloric acid and ethyl acetate to carry out a layer separation operation. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography. To the purified product were added ethyl acetate and hexane, and the resulting solid was collected by filtration and dried to obtain 41 mg of 8-(cyclohexylmethoxy)-2-methyl-N-{(1S)-3-[(methylsulfonyl)amino]-3-oxo-1-phenylpropyl}imidazolo[1,2-a]pyridine-3-carboxamide.

後処理

  1. stirringby stirring for 5 hours
  2. customa layer separation operation
  3. washThe obtained organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography
  7. additionTo the purified product were added ethyl acetate and hexane
  8. filtrationthe resulting solid was collected by filtration
  9. customdried

出典と根拠

ORDレコード
ord-0d0f40036fac45d5b47641f3a632f07c
出典データセット
uspto-grants-2016_09
特許番号
US09447090B2

反応ノート

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