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Diisopropylethylamine → HCID 71285950、化合物

HRID 246224
ノート
印刷プレビュー

反応式

HRID 246224 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

HCID 71285950
HCID 71285950、化合物
収率 80%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-310137dbb53844ae85cfd456fd725203
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08658646B2

反応ノート

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