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

Sodium triacetoxyborohydride → 6-(5-((2-(dimethylphosphinoyl)ethylamino)methyl)furan-2-yl)-N-(1-(3-fluorobenzyl)-1H-indazol-5-yl)quinazolin-4-amine

HRID 877111
노트
인쇄 미리보기

반응식

HRID 877111 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:26]5[O:30][C:29]([CH:31]=O)=[CH:28][CH:27]=5)[CH:24]=4)[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1.[CH3:36][P:37]([CH3:42])([CH2:39][CH2:40][NH2:41])=[O:38].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C>[CH3:36][P:37]([CH3:42])([CH2:39][CH2:40][NH:41][CH2:31][C:29]1[O:30][C:26]([C:23]2[CH:24]=[C:25]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][N:17]=[C:16]3[NH:15][C:11]2[CH:10]=[C:9]3[C:14](=[CH:13][CH:12]=2)[N:6]([CH2:5][C:4]2[CH:33]=[CH:34][CH:35]=[C:2]([F:1])[CH:3]=2)[N:7]=[CH:8]3)=[CH:27][CH:28]=1)=[O:38]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 215271022-(Dimethylphosphinoyl)ethanamine2회HCID 866684795-(4-(1-(3-fluorobenzyl)-1H-indazol-5-ylamino)quinazolin-6-yl)furan-2-carbaldehyde

생성물 1

HCID 498564386-(5-((2-(dimethylphosphinoyl)ethylamino)methyl)furan-2-yl)-N-(1-(3-fluorobenzyl)-1H-indazol-5-yl)quinazolin-4-amine수율 43%

시약·촉매·용매 2

HCID 176
Acetic Acid
촉매
HCID 6344Dichloromethane용매

실험 절차

5-(4-(1-(3-fluorobenzyl)-1H-indazol-5-ylamino)quinazolin-6-yl)furan-2-carbaldehyde and 2-(dimethylphosphinoyl)ethanamine (compound 2.2, 82 mg) were suspended in dichloromethane (20 mL). Sequentially, acetic acid (3 drops) and sodium triacetoxyborohydride (237 mg) were added at room temperature. The mixture was stirred at room temperature until the starting material disappeared. The reaction was quenched with 2N NaOH aqueous solution and extracted with dichloromethane. The combined organic layer and extracts were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography, eluting with 20% methanol in dichloromethane to give the desired product as yellow crystalline solid (138 mg). LCMS ESI(+) m/z: 569 (M+1). Yield: 43%. 1H NMR (300 MHz, CD3OD) δ 8.75 (d, 1H), 8.40 (s, 1H), 8.18 (m, 1H), 8.12 (m, 2H), 7.76 (m, 1H), 7.68 (m, 1H), 7.61 (m, 1H), 7.30 (m, 2H), 7.03 (m, 2H), 6.92 (m, 3H), 6.46 (d, 1H), 5.69 (s, 2H), 3.91 (s, 2H), 2.99 (m, 2H), 2.10 (m, 2H), 1.52 (d, 3H).

후처리

  1. customThe reaction was quenched with 2N NaOH aqueous solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layer and extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 20% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-5895aeecb1fb41bab48105478258e9bd
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08987284B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트