Methyl 3-amino-4-methylbenzoate → Methyl 3-[(1-chloro-9-fluorobenzo[c]-2,6-naphthyridin-5-yl)amino]-4-methylbenzoate

HRID 1802466ノート

反応式

HRID 1802466 の反応式
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[N:6]=[C:7]2Cl.[NH2:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:22]([O:24][CH3:25])=[O:23].CC(C)([O-])C.[Na+]>C1COCC1>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[N:6]=[C:7]2[NH:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:22]([O:24][CH3:25])=[O:23]

参加物

5

反応物 3

HCID 337778Methyl 3-amino-4-methylbenzoateHCID 23676156Sodium t-butoxideHCID 594361181,5-Dichloro-9-fluorobenzo[c]-2,6-naphthyridine

生成物 1

HCID 59436117Methyl 3-[(1-chloro-9-fluorobenzo[c]-2,6-naphthyridin-5-yl)amino]-4-methylbenzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1,5-dichloro-9-fluorobenzo[c]-2,6-naphthytidine (Example 1, Step 5) (500 mg, 1.87 mmol) and methyl 3-amino-4-methylbenzoate (340 mg, 2.06 mmol) in THF (9.3 mL) was added sodium tert-butoxide (396 mg, 4.12 mmol). The reaction stirred at room temperature for ten minutes and was then quenched by the addition of sat. aq. NaHCO3 solution. The mixture was extracted with EtOAc and the extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by silica gel column chromatography (0-30% EtOAc/heptane) afforded the title compound.

後処理

  1. customwas then quenched by the addition of sat. aq. NaHCO3 solution
  2. extractionThe mixture was extracted with EtOAc
  3. washthe extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel column chromatography (0-30% EtOAc/heptane)

出典と根拠

ORDレコード
ord-13067376039147abb3299da62522dbba
出典データセット
uspto-grants-2013_01
特許番号
US08349865B2

反応ノート

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