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Diisopropylethylamine → 2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-methoxy-3-methyl-indol-1-yl)-amide

HRID 2382024
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HRID 2382024 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([CH3:14])[C:11]([C:15]([OH:17])=O)=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.CN(C(SC1[N+]([O-])=CC=CC=1)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:49][O:50][C:51]1[CH:52]=[C:53]2[C:57](=[CH:58][CH:59]=1)[N:56]([NH2:60])[CH:55]=[C:54]2[CH3:61]>O.CCOC(C)=O.CN(C=O)C>[CH3:49][O:50][C:51]1[CH:52]=[C:53]2[C:57](=[CH:58][CH:59]=1)[N:56]([NH:60][C:15]([C:11]1[C:12]([CH3:14])=[N:13][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:9][CH:10]=1)=[O:17])[CH:55]=[C:54]2[CH3:61]
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참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 10571248(Dimethylamino)-N,N-dimethyl((1-oxo-1lambda~5~-pyridin-2-yl)sulfanyl)methaniminium hexafluorophosphateHCID 617025872-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acidHCID 685548125-Methoxy-3-methyl-indol-1-ylamine

생성물 1

HCID 591999882-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-methoxy-3-methyl-indol-1-yl)-amide
수율 32.3%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
23 °C

실험 절차

A microwave vial (20 mL) is charged with 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (657 mg, 2.83 mmol), HOTT (1.16 g, 3.11 mmol), DIPEA (1.35 mL, 7.73 mmol) and DMF (6 mL). The mixture is stirred at 23° C. under N2 for 15 min. 5-Methoxy-3-methyl-indol-1-ylamine (456 mg, 2.59 mmol) is added and the vial is capped. The resulting mixture is heated in a microwave (Biotage-Initiator) at 150° C. for 6 min. The mixture is portioned between EtOAc and water. The organic phase is separated, washed with saturated aqueous NaHCO3, water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by column chromatography eluting with 45% EtOAc in heptane to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-methoxy-3-methyl-indol-1-yl)-amide (327 mg, 32%) as a solid. MS: 391 (M+H); 1H NMR (300 MHz, d6-DMSO): δ 11.75 (s, 1H), 9.19 (s, 1H), 8.32 (d, 1H), 8.18-8.16 (m, 1H), 7.66-7.62 (m, 1H), 7.45 (td, 1H), 7.30 (d, 1H), 7.22 (s, 1H), 7.05 (d, 1H), 6.85 (dd, 1H), 3.81 (s, 3H), 2.76 (s, 3H), 2.27 (s, 3H).

후처리

  1. customthe vial is capped
  2. temperatureThe resulting mixture is heated in a microwave (Biotage-Initiator) at 150° C. for 6 min
  3. customThe organic phase is separated
  4. washwashed with saturated aqueous NaHCO3, water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography
  9. washeluting with 45% EtOAc in heptane

출처 및 근거

ORD 기록
ord-517eb4b213394e8895a75a33e593d0f4
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08258130B2

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