Tetrahydrofuran → HCID 11713729、化合物

HRID 1867617ノート

反応式

HRID 1867617 の反応式
[NH2:1][C@@H:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][C:20]([F:23])([F:22])[F:21])[C:3]1=[O:24].C(N(CC)CC)C.[O:32]=[C:33]1[NH:37][C:36]([C:38]#[N:39])=[CH:35][N:34]1[CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.[O:46]1CCC[CH2:47]1>>[C:38]([C:36]1[NH:37][C:33](=[O:32])[N:34]([CH:40]2[CH2:45][CH2:44][N:43]([C:47]([NH:1][C@@H:2]3[N:8]=[C:7]([C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:6]4[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=4[N:4]([CH2:19][C:20]([F:21])([F:23])[F:22])[C:3]3=[O:24])=[O:46])[CH2:42][CH2:41]2)[CH:35]=1)#[N:39]

参加物

5

反応物 4

HCID 8028TetrahydrofuranHCID 8471Triethylamine2 回HCID 10854086HCID 10854086、化合物HCID 598565282-Oxo-1-piperidin-4-yl-2,3-dihydro-1H-imidazole-4-carbonitrile

生成物 1

HCID 11713729HCID 11713729、化合物

実験手順

(3R)-3-Amino-5-phenyl-1-(2,2,2-trifluoroethyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one (38 mg, 0.114 mmol) (Y.-J. Shi et al., Tetrahedron, 1999, 55, 909-918) and triethylamine (0.017 mL, 0.120 mmol) were added to a solution of p-nitrophenylchloroformate (23 mg, 0.114 mmol) in tetrahydrofuran (15 mL) at 0 oC. After 1 h, 2-oxo-1-piperidin-4-yl-2,3-dihydro-1H-imidazole-4-carbonitrile (23 mg, 0.120 mmol) and additional triethylamine (0.034 μL, 0.240 mmol) were added. The reaction warmed to ambient temperature and was then heated to 50 oC. After 2 h, the reaction was concentrated and then partitioned between dichloromethane and saturated sodium bicarbonate. The organics were washed with water, brine, and dried over magnesium sulfate. Purification by silica gel chromatography (100% dichloromethane→7% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound (40 mg). MS 552.195 (M+1)

後処理

  1. temperaturewas then heated to 50 oC
  2. waitAfter 2 h
  3. concentrationthe reaction was concentrated
  4. custompartitioned between dichloromethane and saturated sodium bicarbonate
  5. washThe organics were washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. customPurification by silica gel chromatography (100% dichloromethane→7% methanol {1% ammonium hydroxide}/dichloromethane)

出典と根拠

ORDレコード
ord-1fbfb7b0e31f4068836619a2bd9baf60
出典データセット
uspto-grants-2009_12
特許番号
US07632832B2

反応ノート

読み込み中…