Sodium hydride → HCID 53262117、化合物

HRID 1509154ノート

反応式

HRID 1509154 の反応式
C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:20][C:21]4[NH:26][C:25](=[O:27])[CH2:24][O:23][C:22]=4[N:28]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.[H-].[Na+].Br[CH2:39][CH:40]1[CH2:43][CH2:42][CH2:41]1.C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:20][C:21]4[N:26]([CH2:39][CH:40]5[CH2:43][CH2:42][CH2:41]5)[C:25](=[O:27])[CH2:24][O:23][C:22]=4[N:28]=3)=[CH:14][CH:13]=2)[CH2:9][CH2:10][CH2:11]1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 2734658(Bromomethyl)cyclobutaneHCID 67256382HCID 67256382、化合物

生成物 1

HCID 53262117HCID 53262117、化合物収率 20.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of tert-butyl(1-(4-(2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (44 mg, 0.09 mmol) in dry DMF (1 ml) was added sodium hydride (9 mg, 0.22 mmol) and (bromomethyl)cyclobutane (130, 0.11 mmol) under nitrogen. The resulting mixture was stirred for 1 h at 80 C. A saturated solution of NaHCO3 was added and the mixture was extracted with dichloromethane (3×10 ml) using a phase separator (Isolute® SPE). The combined organic phases were concentrated to dryness under reduced pressure. The resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 40% EtOAc in cyclohexane) to give the title compound (8 mg, 16%). 1H NMR (500 MHz, CDCl3): 7.23-7.17 (8H, m), 7.13-7.11 (2H, m), 4.95 (1H, s), 4.80 (2H, s), 3.96 (2H, d), 2.68-2.64 (1H, m), 2.52-2.20 (4H, m), 2.00-1.95 (3H, m), 1.86-1.50 (5H, m), 1.44-1.15 (9H, br).

後処理

  1. extractionthe mixture was extracted with dichloromethane (3×10 ml)
  2. concentrationThe combined organic phases were concentrated to dryness under reduced pressure
  3. customThe resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 40% EtOAc in cyclohexane)

出典と根拠

ORDレコード
ord-0cecd67d431648009763eab0a155068d
出典データセット
uspto-grants-2015_12
特許番号
US09221838B2

反応ノート

読み込み中…