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Diisopropylethylamine → HCID 71285950, 화합물

HRID 246224
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HRID 246224 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21](O)=[O:22])=[CH:19][N:18]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[Br:57][C:58]1[CH:59]=[C:60]([C:64]2([NH2:68])[CH2:67][CH2:66][CH2:65]2)[CH:61]=[CH:62][CH:63]=1.CCN(C(C)C)C(C)C>CN(C=O)C.O.CC(=O)OCC>[Br:57][C:58]1[CH:59]=[C:60]([C:64]2([NH:68][C:21]([C:20]3[C:14]4[C:15](=[N:16][CH:17]=[C:12]([C:6]5[C:5]6[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=6)[N:8]([CH3:11])[N:7]=5)[N:13]=4)[N:18]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:30])([CH3:31])[CH3:29])[CH:19]=3)=[O:22])[CH2:67][CH2:66][CH2:65]2)[CH:61]=[CH:62][CH:63]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 468355151-(3-Bromophenyl)cyclobutan-1-amine--hydrogen chloride (1/1)HCID 712796202-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

생성물 1

HCID 71285950
HCID 71285950, 화합물
수율 80%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred suspension of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (200 mg, 0.45 mmol) in DMF (5 mL) were added HATU (344 mg, 0.91 mmol) and 1-(3-bromo-phenyl)-cyclobutanamine hydrochloride (178 mg, 0.68 mmol) followed by DIPEA (0.40 mL, 2.26 mmol) at room temperature under nitrogen atmosphere. The resulting light yellow solution was stirred for 15 h by which time TLC analysis (Hex:EA, 1:1, Rf=0.5) indicated the presence of a new spot. Then, the reaction mixture was diluted with water and the organic compound was extracted into EtOAc (3×25 mL). The combined extracts were washed with brine solution and then dried over anhydrous MgSO4. Filtration of the drying agent and concentration of the filtrate gave the crude product which was purified using by ISCO column chromatography (40 g) eluting with EtOAc in hexanes (0-60%) in 10 minutes. The desired fractions were combined and the solvent was removed under vacuum to obtain 234 mg (80%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [1-(3-bromophenyl)-cyclobutyl]-amide as a light brown solid.

후처리

  1. extractionthe organic compound was extracted into EtOAc (3×25 mL)
  2. washThe combined extracts were washed with brine solution
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationFiltration of the drying agent and concentration of the filtrate
  5. customgave the crude product which
  6. customwas purified
  7. washeluting with EtOAc in hexanes (0-60%) in 10 minutes
  8. customthe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-310137dbb53844ae85cfd456fd725203
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658646B2

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