Diisopropylethylamine → HCID 59200056, 화합물

HRID 2382083노트

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HRID 2382083 반응식
[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([NH2:12])[CH:4]=1)[CH3:2].[F:13][C:14]1[CH:15]=[C:16]([C:20]2[N:25]=[C:24]([CH3:26])[C:23]([C:27](O)=[O:28])=[CH:22][N:21]=2)[CH:17]=[CH:18][CH:19]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([NH:12][C:27]([C:23]2[C:24]([CH3:26])=[N:25][C:20]([C:16]3[CH:17]=[CH:18][CH:19]=[C:14]([F:13])[CH:15]=3)=[N:21][CH:22]=2)=[O:28])[CH:4]=1)[CH3:2]

참가 물질

6

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 617025872-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acidHCID 68550962HCID 68550962, 화합물

생성물 1

HCID 59200056HCID 59200056, 화합물수율 43.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

A mixture of 3-ethyl-pyrrolo[2,3-b]pyridin-1-ylamine (126 mg, 0.78 mmol), 2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (180 mg, 0.78 mmol), HATU (356 mg, 0.036 mmol) and DIPEA (302 mg, 2.34 mmol) in DMF (4 mL) is heated at 150° C. for 1 h. The reaction is quenched with water and extracted with EtOAc. The organic layer is dried (Na2SO4), filtered and concentrated. The residue is chromatographed through silica gel eluting with 0-100% ethyl acetate in heptane to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-ethyl-pyrrolo[2,3-b]pyridin-1-yl)-amide (128 mg). MS: 376 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 9.10 (s, 1H), 8.25-8.33 (m, 2H), 8.16 (d, 1H), 8.05 (d, 1H), 7.62 (q, 1H), 7.39-7.48 (m, 2H), 7.16 (dd, 1H), 2.78 (s, 3H), 2.75 (q, 2H), 1.29(t, 3H).

후처리

  1. customThe reaction is quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed through silica gel eluting with 0-100% ethyl acetate in heptane

출처 및 근거

ORD 기록
ord-89ffca78f22a44399761336ee44b50c4
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258130B2

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