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Acrylonitrile → (+/-)-trans-3-{[3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexyl]-oxy}propanenitrile

HRID 2189049
ノート
印刷プレビュー

反応式

HRID 2189049 の反応式
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:22]([NH:24][C@H:25]4[CH2:30][CH2:29][CH2:28][C@H:27]([OH:31])[CH2:26]4)=[N:21][CH:20]=[N:19][C:18]=3[O:17][C:16]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:11][CH:10]=1.[C:38](#[N:41])[CH:39]=[CH2:40]>C1COCC1.ClCCl>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:23]3[C:22]([NH:24][C@H:25]4[CH2:30][CH2:29][CH2:28][C@H:27]([O:31][CH2:40][CH2:39][C:38]#[N:41])[CH2:26]4)=[N:21][CH:20]=[N:19][C:18]=3[O:17][C:16]=2[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:13][CH:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 7855AcrylonitrileHCID 23665647Potassium tert-butoxideHCID 58280259trans-3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexanol

生成物 1

HCID 58280115(+/-)-trans-3-{[3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexyl]-oxy}propanenitrile

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

Add a solution of approx. 2 mg of potassium tert-butoxide in 0.2 ml of THF dropwise to a solution of 34.4 mg (0.059 mmol) of (+/−)-trans-3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexanol in 0.23 ml of acrylonitrile. Stir the reaction mixture with exclusion of light at RT for approx. 2 h. After diluting with dichloromethane, wash successively with 1N hydrochloric acid, satd. sodium hydrogencarbonate solution and satd. sodium chloride solution, and concentrate the organic phase under reduced pressure. After the residue has been purified by means of preparative RP-HPLC (eluent: acetonitrile/water gradient), 33.6 mg of the target product are obtained (86.6% of theory).

後処理

  1. washwash successively with 1N hydrochloric acid
  2. concentrationsodium chloride solution, and concentrate the organic phase under reduced pressure
  3. customAfter the residue has been purified by means of preparative RP-HPLC (eluent: acetonitrile/water gradient), 33.6 mg of the target product
  4. customare obtained (86.6% of theory)

出典と根拠

ORDレコード
ord-25c7042d9b374561af9c6b6abab5c0b8
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08324222B2

反応ノート

読み込み中…

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