Dimethylformamide → HCID 86683573, 화합물

HRID 1509146노트

반응식

HRID 1509146 반응식
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:20][C:21]4[NH:26][CH2:25][CH2:24][O:23][C:22]=4[N:27]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])(C)C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:42][C:43]#N.[C:45]([O-])(O)=O.[Na+].C[N:51]([CH:53]=O)C>>[C:53]([CH2:45][N:26]1[CH2:25][CH2:24][O:23][C:22]2[N:27]=[C:18]([C:15]3[CH:14]=[CH:13][C:12]([C:8]4([NH:7][C:6](=[O:34])[O:5][CH2:1][CH2:4][CH2:42][CH3:43])[CH2:11][CH2:10][CH2:9]4)=[CH:17][CH:16]=3)[C:19]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:20][C:21]1=2)#[N:51]

참가 물질

6

반응물 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 516892Sodium BicarbonateHCID 123843496HCID 123843496, 화합물

생성물 1

HCID 86683573HCID 86683573, 화합물수율 19%

실험 절차

To a solution of tert-butyl(1-(4-(7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (24 mg, 0.05 mmol) in dry DMF (1 ml) was added potassium carbonate (93 mg, 1.57 mmol) and bromoacetonitrile (110 μl, 1.57 mmol) under nitrogen. The resulting mixture was stirred for 4 hours 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 60% EtOAc in cyclohexane) to give the title compound (5 mg, 19%). 1H NMR (500 MHz, CDCl3): 7.22-7.11 (9H, m), 6.93 (1H, s), 4.92 (1H, s), 4.51-4.49 (2H, m), 4.15 (2H, s), 3.39-3.37 (2H, m), 2.55-2.25 (4H, m), 1.99-1.94 (1H, m), 1.75-1.63 (1H, m), 1.44-1.15 (9H, br).

후처리

  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 60% EtOAc in cyclohexane)

출처 및 근거

ORD 기록
ord-b8e8b36bf0504b23b3bb72720aafa5b8
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221838B2

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