Diisopropylethylamine → 4'-Fluoro-biphenyl-4-carboxylic acid [2-(3-dimethylamino-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide

HRID 1174921ノート

反応式

HRID 1174921 の反応式
[CH3:1][N:2]([CH3:18])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:11]=3[N:12]=2)[CH2:4]1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=2)=[CH:22][CH:21]=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>C(Cl)Cl>[CH3:1][N:2]([CH3:18])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([NH:17][C:30]([C:29]4[CH:28]=[CH:27][C:26]([C:23]5[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=5)=[CH:34][CH:33]=4)=[O:31])=[CH:13][C:11]=3[N:12]=2)[CH2:4]1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 27826894-(4-Fluorophenyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 687717302-(3-Dimethylamino-pyrrolidin-1-yl)-benzooxazol-5-ylamine

生成物 1

HCID 766013434'-Fluoro-biphenyl-4-carboxylic acid [2-(3-dimethylamino-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide収率 77.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Combine 2-(3-dimethylamino-pyrrolidin-1-yl)-benzooxazol-5-ylamine (0.100 g, 0.406 mmol), 4-(4-fluorophenyl)benzoic acid (0.073 g, 0.338 mmol), and HATU (0.129 g, 0.338 mmol) in CH2Cl2 and add DIEA (0.18 mL, 1.01 mmol). Shake the mixture in a shaker block at 40° C. for 72 h. Dilute the reaction mixture with CH2Cl2 (30 mL), and wash with saturated NaHCO3 (aqueous) (2×25 mL). Dry the organic phase over anhydrous sodium sulfate, filter, and concentrate in vacuo. Subject the crude product to flash column chromatography (40 g column) eluting with 8% MeOH/CH2Cl2, to yield the title compound as a bluish-white solid (0.116 g, 65%). mass spectrum (m/e): 445.3 [M+1], 443.3 [M−1]. 1H NMR (400 MHz, DMSO-d6): δ 10.23 (s, 1H), 8.05 (d, 2H, J=8.4 Hz), 7.85-7.79 (m, 4H), 7.75 (d, 1H, J=2.2 Hz), 7.41-7.30 (m, 4H), 3.79 (dd, 1H, J=9.9, 7.1 Hz), 3.72 (m, 1H), 3.54 (m, 1H), 3.31 (m, 1H), 2.86 (m, 1H), 2.25-2.12 (m, 7H), 1.86 (m, 1H).

後処理

  1. washwash with saturated NaHCO3 (aqueous) (2×25 mL)
  2. dry with materialDry the organic phase over anhydrous sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. washeluting with 8% MeOH/CH2Cl2

出典と根拠

ORDレコード
ord-6cd2e36e257c4dbc97ea84c360779d5b
出典データセット
uspto-grants-2010_11
特許番号
US07838543B2

反応ノート

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