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Diisopropylethylamine → 2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-fluoro-3,3-dimethyl-2,3-dihydro-indol-1-yl)-amide

HRID 2381914
ノート
印刷プレビュー

反応式

HRID 2381914 の反応式
[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.[F:49][C:50]1[CH:51]=[C:52]2[C:56](=[CH:57][CH:58]=1)[N:55]([NH2:59])[CH2:54][C:53]2([CH3:61])[CH3:60]>CN(C=O)C.O.CCOC(C)=O>[F:49][C:50]1[CH:51]=[C:52]2[C:56](=[CH:57][CH:58]=1)[N:55]([NH:59][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])[CH2:54][C:53]2([CH3:61])[CH3:60]
参加物反応条件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 10571248(Dimethylamino)-N,N-dimethyl((1-oxo-1lambda~5~-pyridin-2-yl)sulfanyl)methaniminium hexafluorophosphateHCID 617025872-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acidHCID 68555288HCID 68555288、化合物

生成物 1

HCID 250995182-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-fluoro-3,3-dimethyl-2,3-dihydro-indol-1-yl)-amide
収率 80%

試薬・触媒・溶媒 3

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

反応条件

温度
80 °C

実験手順

A solution of 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (348 mg, 1.5 mmol), HOTT (618 mg, 1.66 mmol), and DIPEA (700 μL, 4.01 mmol) in DMF (10 mL) is stirred at rt under N2 for 10 min. 5-Fluoro-3,3-dimethyl-2,3-dihydro-indol-1-ylamine (239 mg, 1.33 mmol) is added. The resulting mixture is stirred at 80° C. overnight. The mixture is cooled and 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 silica gel chromatography eluting with 15% EtOAc in heptane to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-fluoro-3,3-dimethyl-2,3-dihydro-indol-1-yl)-amide (416 mg, 80%) as a solid. MS: 395 (M+H). 1H NMR (300 MHz, DMSO-d6): δ 10.43 (s, 1H), 8.99 (s, 1H), 8.28 (d, 1H), 8.15-8.11 (m, 1H), 7.66-7.58 (m, 1H), 7.46-7.39 (m, 1H), 7.06 (dd, 1H), 6.95-6.88 (m, 1H), 6.75-6.71 (m, 1H), 3.51 (s, 2H), 2.68 (s, 3H), 1.33 (s, 6H).

後処理

  1. temperatureThe mixture is cooled
  2. customThe organic phase is separated
  3. washwashed with saturated aqueous NaHCO3, water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with 15% EtOAc in heptane

出典と根拠

ORDレコード
ord-c9237b38f1834f9c93b02258275a21f4
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08258130B2

反応ノート

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