Sodium Carbonate → HCID 178455121, 화합물

HRID 1807625노트

반응식

HRID 1807625 반응식
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][N:17]=1)[C:13]#[N:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.[NH2:19][OH:20].C([O-])([O-])=O.[Na+].[Na+]>CCO>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][N:17]=1)[C:13](=[NH:14])[NH:19][OH:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 583550752-((Tert-butyldimethylsilyloxy)methyl)isonicotinonitrile

생성물 1

HCID 178455121HCID 178455121, 화합물수율 100%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
85 °C

실험 절차

Prepared using General Procedure 1. To 2-((tert-butyldimethylsilyloxy)methyl)isonicotinonitrile INT-71 (0.169 g, 0.68 mmol) in EtOH (8 mL) was added hydroxylamine hydrochloride (0.142 g, 2.0 mmol) and Na2CO3 (0.216 g, 2.0 mmol) and the reaction mixture was heated at 85° C. for 12 h. Once cooled to room temperature, the reaction mixture was filtered using EtOH to rinse the filter cake. The filtrate was concentrated under reduced pressure and washed with EA and brine. The combined organic layers were dried over MgSO4, filtered, and concentrated to produce 0.191 g (100%) of 2-((tert-butyldimethylsilyloxy)methyl)-N-hydroxyisonicotinimidamide INT-72 as a light yellow oil. LCMS-ESI (m/z) calculated for C13H23N3O2Si: 281.4; found 282.1 [M+H]+, tR=2.76 min (Method 1). 1H NMR (400 MHz, (CD3)2SO) δ 8.50 (dd, J=5.2, 0.7, 1H), 7.74 (dd, J=1.6, 0.7, 1H), 7.51 (dd, J=5.2, 1.7, 1H), 5.98 (s, 2H), 0.96-0.89 (m, 9H), 0.14-0.07 (m, 6H).

후처리

  1. customPrepared
  2. temperatureOnce cooled to room temperature
  3. filtrationthe reaction mixture was filtered
  4. washto rinse the filter cake
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washwashed with EA and brine
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a49c24193e514544b372ca7f430d9cb8
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08357706B2

반응 노트

불러오는 중…