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

Diisopropylethylamine → (S)-5-(4-aminophenylthio)-4-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)-N-(2-phenylpropyl)thiophene-2-carboxamide

HRID 605377
노트
인쇄 미리보기

반응식

HRID 605377 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[S:13][C:12]([C:14](O)=[O:15])=[CH:11][C:10]=2[NH:17][C:18]2[C:19]3[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[N:24][C:20]=3[N:21]=[CH:22][N:23]=2)=[CH:4][CH:3]=1.[CH3:31][C@@H:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:33][NH2:34].C(N(CC)C(C)C)(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CS(C)=O.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[S:13][C:12]([C:14]([NH:34][CH2:33][C@H:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH3:31])=[O:15])=[CH:11][C:10]=2[NH:17][C:18]2[C:19]3[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[N:24][C:20]=3[N:21]=[CH:22][N:23]=2)=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 1547950(2S)-2-Phenylpropan-1-amineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 670411655-(4-Aminophenylthio)-4-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)thiophene-2-carboxylic acid

생성물 1

HCID 25117305(S)-5-(4-aminophenylthio)-4-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)-N-(2-phenylpropyl)thiophene-2-carboxamide
수율 85.2%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

The product of Example 430F (62 mg, 0.142 mmol) in dimethyl sulfoxide (2 mL) under a nitrogen atmosphere was reacted with (S)-(−)-β-methylphenethylamine (23 mg, 0. 170 mmol), N,N-diisopropylethylamine (0.123 mL, 0.708 mmol), and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (55 mg, 0.170 mmol at room temperature for 20 hours. The reaction mixture was diluted with water (10 mL), and extracted with ethyl acetate (50 mL). The organic extract was washed sequentially with water (3×10 mL), saturated aqueous sodium hydrogencarbonate (20 mL), and brine (20 mL), dried over magnesium sulfate, filtered, and concentrated by rotary evaporation. Purification of the residue by silica gel flash chromatography eluting with 4:96 methanol/methylene chloride afforded the title compound (67 mg, 0.121 mmol, 85%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.19 (d, J=6.99 Hz, 3 H) 1.33 (d, J=6.99 Hz, 6 H) 2.91-3.07 (m, 1 H) 3.14-3.29 (m, 1 H) 5.50 (s, 2 H) 6.51 (d, J=8.46 Hz, 2 H) 7.12 (d, J=8.82 Hz, 2 H) 7.16-7.34 (m, 5 H) 7.63 (d, J=8.46 Hz, 1 H) 7.77 (s, 1 H) 8.50 (t, J=5.88 Hz, 1 H) 8.62 (s, 1 H) 8.82 (d, J=8.82 Hz, 1 H) 9.97 (s, 1 H); MS (ESI+) m/z 555 (M+H)+, 1109 (2M+H)+, MS (ESI−) m/z 553 (M−H)−.

후처리

  1. extractionextracted with ethyl acetate (50 mL)
  2. extractionThe organic extract
  3. washwas washed sequentially with water (3×10 mL), saturated aqueous sodium hydrogencarbonate (20 mL), and brine (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. customPurification of the residue by silica gel flash chromatography
  8. washeluting with 4:96 methanol/methylene chloride

출처 및 근거

ORD 기록
ord-2926189f8fe04647bfabc78ae2f47031
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07910595B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트