Acetic Acid → 7-(cyclohexylamino)-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one

HRID 1753178ノート

反応式

HRID 1753178 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:8]3[CH2:11][CH2:12][N:13]([C:14]([C:16]4[C:17]([CH3:21])=[N:18][O:19][CH:20]=4)=[O:15])[C:7]3([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[CH2:6][N:5]2[CH:30]=1.[C:31]1(=O)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:31]1([NH:1][C:2]2[CH:3]=[C:4]3[C:9](=[O:10])[N:8]4[CH2:11][CH2:12][N:13]([C:14]([C:16]5[C:17]([CH3:21])=[N:18][O:19][CH:20]=5)=[O:15])[C:7]4([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[CH2:6][N:5]3[CH:30]=2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

参加物

6

反応物 4

HCID 176Acetic Acid2 回HCID 7967Cyclohexanone2 回HCID 5049666Sodium triacetoxyborohydrideHCID 533733037-amino-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]-pyrazin-5-one

生成物 1

HCID 584063677-(cyclohexylamino)-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 7-amino-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]-pyrazin-5-one (33 mg, 0.081 mmol) in CH2Cl2 (0.5 mL) was added cyclohexanone (9 μL, 0.081 mmol), acetic acid (7 μL, 0.12 mmol) followed by sodium triacetoxyborohydride (26 mg, 0.12 mmol). After stirring the mixture for three further hours, cyclohexanone (20 μL, 0.18 mmol) was added followed by the addition of additional acetic acid (20 μL, 0.34 mmol). The mixture was quenched with a saturated aqueous solution of NaHCO3. Additional CH2Cl2 (3 mL) was added and the organic layer separated, the aqueous layer was further extracted with CH2Cl2 (3 mL). The organic layers were combined dried (Na2SO4), filtrated, concentrated in vacuo to give a residue that was purified by flash chromatography (Biotage SP4, gradient 0-10% MeOH in EtOAc) and reverse phase chromatography (Biotage SP4, 12 g C18 cartridge; gradient ACN in water). The compound 7-(cyclohexylamino)-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (112) was isolated as a solid (1.6 mg, yield 1%).

後処理

  1. additionwas added
  2. customThe mixture was quenched with a saturated aqueous solution of NaHCO3
  3. additionAdditional CH2Cl2 (3 mL) was added
  4. customthe organic layer separated
  5. extractionthe aqueous layer was further extracted with CH2Cl2 (3 mL)
  6. dry with materialThe organic layers were combined dried (Na2SO4)
  7. filtrationfiltrated
  8. concentrationconcentrated in vacuo
  9. customto give a residue that
  10. customwas purified by flash chromatography (Biotage SP4, gradient 0-10% MeOH in EtOAc)

出典と根拠

ORDレコード
ord-f305975d334a40c6863c6da5f6352453
出典データセット
uspto-grants-2015_10
特許番号
US09163029B2

反応ノート

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