홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Sodium Chloride → Tetramethylurea

HRID 408790
노트
인쇄 미리보기

반응식

HRID 408790 반응식
Cl.[Br:2][C:3]1[N:7]2[C:8]([CH3:12])=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:13]([OH:15])=O.[Cl-].[Na+].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.[N:34]1([O:43][C:44]([N:48]([CH3:50])[CH3:49])=[N+:45]([CH3:47])[CH3:46])[C:38]2C=CC=CC=2N=N1.Cl.CNOC.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Br:2][C:3]1[N:7]2[C:8]([CH3:12])=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:13]([N:34]([O:43][CH3:44])[CH3:38])=[O:15].[CH3:46][N:45]([CH3:47])[C:44](=[O:43])[N:48]([CH3:50])[CH3:49]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 6

HCID 5234Sodium ChlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 672575653-Bromo-5-methylimidazo[1,2-a]pyridine-2-carboxylic acid hydrochloride

생성물 2

HCID 12437TetramethylureaHCID 583793113-bromo-N-methoxy-N,5-dimethylimidazo[1,2-a]pyridine-2-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
20 °C

실험 절차

A solution of 3-bromo-5-methylimidazo[1,2-a]pyridine-2-carboxylic acid hydrochloride (0.63 g, 2.2 mmol) (this material contained sodium chloride from the previous step) in N,N-dimethylformamide (6 mL) was treated with N,N-diisopropylethylamine (1.9 mL, 11 mmol) followed by O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate and stirred at 20° C. for 5 min. The reaction mixture was treated with N,O-dimethylhydroxylamine hydrochloride (0.28 g, 2.8 mmol) and stirred at 20° C. for 2 h. The reaction mixture was poured into saturated sodium bicarbonate (100 mL) and extracted with ethyl acetate (100 mL). The aqueous phase was separated, saturated with sodium chloride, and extracted with additional ethyl acetate (100 mL). The combined organic extracts were washed with brine (100 mL), dried with sodium sulfate, filtered, and concentrated to a crude oil. Purification by flash column chromatography gave the desired product that also contained N,N-dimethylformamide and tetramethyl urea. This material was diluted with ethyl acetate (100 mL), washed with water (50 mL) and brine (20 mL), dried with sodium sulfate, filtered, and concentrated to give 0.55 g of the desired product as a white solid. The aqueous layer, which still contained desired product, was concentrated and the resultant residue was purified by preparative LCMS to give an additional 42 mg of the desired product. The total amount isolated was 0.59 g (91%). LCMS for C11H13BrN3O2 (M+H)+: m/z=298.0, 300.0.

후처리

  1. stirringstirred at 20° C. for 2 h
  2. extractionextracted with ethyl acetate (100 mL)
  3. customThe aqueous phase was separated, saturated with sodium chloride
  4. extractionextracted with additional ethyl acetate (100 mL)
  5. washThe combined organic extracts were washed with brine (100 mL)
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to a crude oil
  9. customPurification by flash column chromatography

출처 및 근거

ORD 기록
ord-98c2946a021d4b2193c32dd74c4f6056
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08759359B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트