Methylamine → 2-Chloro-6-[4-(methylamino)piperidin-1-yl]isonicotinonitrile

HRID 2233856ノート

反応式

HRID 2233856 の反応式
CN.[Cl:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)[N:11]=1)[C:7]#[N:8].ClC1C=C(C=C(N2CCC(O)CC2)N=1)[C:23]#[N:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([NH:24][CH3:23])[CH2:14][CH2:13]2)[N:11]=1)[C:7]#[N:8]

参加物

6

反応物 4

HCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 717484322-Chloro-6-(4-oxopiperidin-1-yl)isonicotinonitrileHCID 830734032-Chloro-6-(4-hydroxypiperidin-1-yl)isonicotinonitrile

生成物 1

HCID 860383832-Chloro-6-[4-(methylamino)piperidin-1-yl]isonicotinonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methylamine (2.65 ml, 5.3 mmol) was added to a solution of 2-chloro-6-(4-oxopiperidin-1-yl)isonicotinonitrile (Intermediate 26; 500 mg, 2.12 mmol) in anhydrous THF (4 ml). The mixture was stirred for 30 minutes and sodium triacetoxyborohydride (674 mg, 3.18 mmol) was added. The mixture was stirred at room temperature for 18 h, then concentrated in vacuo, diluted with EtOAc and washed with 1 N NaOH, water and brine. The organic phase was dried over Na2SO4 then concentrated in vacuo to give a brown oil which was dried under vacuum to yield the title compound (507 mg).

後処理

  1. stirringThe mixture was stirred at room temperature for 18 h
  2. concentrationconcentrated in vacuo
  3. additiondiluted with EtOAc
  4. washwashed with 1 N NaOH, water and brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationthen concentrated in vacuo
  7. customto give a brown oil which
  8. customwas dried under vacuum

出典と根拠

ORDレコード
ord-1e6b205f0853498eacce823b37a68b42
出典データセット
uspto-grants-2010_05
特許番号
US07709503B2

反応ノート

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