Tert-Butylamine → N-tert-butyl-2-(5-methoxy-1-methyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246391

반응식

HRID 246391 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][C:26]([NH2:29])([CH3:28])[CH3:27].[CH3:30][O:31][C:32]1[CH:33]=[C:34]2[C:38](=[CH:39][CH:40]=1)[N:37]([CH3:41])[N:36]=[C:35]2[C:42]1[N:43]=[C:44]2[C:50]([C:51](O)=[O:52])=[CH:49][N:48]([CH2:54][O:55][CH2:56][CH2:57][Si:58]([CH3:61])([CH3:60])[CH3:59])[C:45]2=[N:46][CH:47]=1>CN(C=O)C>[C:26]([NH:29][C:51]([C:50]1[C:44]2[C:45](=[N:46][CH:47]=[C:42]([C:35]3[C:34]4[C:38](=[CH:39][CH:40]=[C:32]([O:31][CH3:30])[CH:33]=4)[N:37]([CH3:41])[N:36]=3)[N:43]=2)[N:48]([CH2:54][O:55][CH2:56][CH2:57][Si:58]([CH3:59])([CH3:61])[CH3:60])[CH:49]=1)=[O:52])([CH3:28])([CH3:27])[CH3:25]

참가 물질

5

반응물 3

HCID 6385Tert-ButylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 712798522-(5-methoxy-1-methyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

생성물 1

HCID 71279513N-tert-butyl-2-(5-methoxy-1-methyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide수율 89.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
25 °C

실험 절차

In a 16×100 mm screw cap test tube were added HATU (40.2 mg, 106 μmol.20) and 2-methylpropan-2-amine (25.8 mg, 353 μmol) then 2-(5-methoxy-1-methyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (40 mg, 88.2 mmol) dissolved in DMF (2.00 mL) was added to give a light yellow solution which immediately formed a white precipitated. The reaction mixture stirred at 25° C. overnight, solvents evaporated and residue purified by chromatography (spherical silica 20-45 μm, 23 g, Versaflash Supelco) eluting with 0 to 50% EtOAc in hexanes over 30 min to yield N-tert-butyl-2-(5-methoxy-1-methyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (40 mg, 78.6 μmol, 89.2%) as an off-white solid. MS (M+H)+=509 (>90% purity); 1H NMR (CDCl3) δ: 9.11 (s, 1H), 8.32 (s, 1H), 8.20 (s, 1H), 7.85 (d, J=2.3 Hz, 1H), 7.40 (d, J=9.1 Hz, 1H), 7.20 (dd, J=9.1, 2.3 Hz, 1H), 5.72 (s, 2H), 4.18 (s, 3H), 3.92 (s, 3H), 3.54-3.64 (m, 2H), 1.58 (s, 9H), 0.90-1.01 (m, 2H), −0.03 (s, 9H).

후처리

  1. customIn a 16×100 mm screw cap test tube
  2. additionwas added
  3. customto give a light yellow solution which
  4. customimmediately formed a white precipitated
  5. customsolvents evaporated
  6. customresidue purified by chromatography (spherical silica 20-45 μm, 23 g, Versaflash Supelco)
  7. washeluting with 0 to 50% EtOAc in hexanes over 30 min

출처 및 근거

ORD 기록
ord-4105c66e36d742eba285fc55f611cfbd
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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