Acetic Acid → 1-(2-[(2R)-4-(6-Fluoro-1-naphthyl)-2-methyl-piperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

HRID 2056756ノート

反応式

HRID 2056756 の反応式
O=[CH:2][CH2:3][CH:4]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]#[N:15])=[CH:13][C:8]=2[CH2:7][CH2:6][O:5]1.[F:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23]([N:27]1[CH2:32][CH2:31][NH:30][C@H:29]([CH3:33])[CH2:28]1)=[CH:22][CH:21]=[CH:20]2.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[F:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23]([N:27]1[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH:4]3[C:9]4[CH:10]=[CH:11][C:12]([C:14]#[N:15])=[CH:13][C:8]=4[CH2:7][CH2:6][O:5]3)[C@H:29]([CH3:33])[CH2:28]1)=[CH:22][CH:21]=[CH:20]2

参加物

6

反応物 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydride2 回HCID 69307275(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazineHCID 865960151-(2-Oxoethyl)-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

生成物 1

HCID 693073181-(2-[(2R)-4-(6-Fluoro-1-naphthyl)-2-methyl-piperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of 1-(2-oxoethyl)-3,4-dihydro-1H-2-benzopyran-6-carbonitrile (0.454 g, 2.26 mmol) in methanol (30 mL) was added (3R)-1-(6-fluoro-1-naphthyl)-3-methylpiperazine (0.61 g, 2.49 mmol), and the mixture stirred for 10 min. Sodium cyanoborohydride (0.157 g, 2.49 mmol) and acetic acid (0.25 mL) were added and the mixture stirred for 18 h. A further portion of sodium cyanoborohydride (0.20 g) was added and the reaction stirred for 6 h. The mixture was quenched with water, and the solvent removed in vacuo. Water was added and the mixture extracted with chloroform, the organic extracts dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by preparative LC-MS to yield the title compound as a yellow oil.

後処理

  1. stirringthe mixture stirred for 18 h
  2. stirringthe reaction stirred for 6 h
  3. customThe mixture was quenched with water
  4. customthe solvent removed in vacuo
  5. additionWater was added
  6. extractionthe mixture extracted with chloroform
  7. dry with materialthe organic extracts dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe crude product was purified by preparative LC-MS

出典と根拠

ORDレコード
ord-5903f0d05655498882700973ba6bf066
出典データセット
uspto-grants-2008_02
特許番号
US07335660B2

反応ノート

読み込み中…