Diisopropylethylamine → HCID 58447638、化合物

HRID 592254ノート

反応式

HRID 592254 の反応式
[S:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=O)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[F:17][C:18]1[CH:19]=[C:20]([C:24]2[N:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[CH:21]=[CH:22][CH:23]=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.C(OCC)(=O)C.O>[F:17][C:18]1[CH:19]=[C:20]([C:24]2[N:29]=[CH:28][C:27]([NH:30][C:14](=[O:16])[CH2:13][C:10]3[CH:11]=[N:12][C:7]([N:4]4[CH2:3][CH2:2][S:1][CH2:6][CH2:5]4)=[CH:8][CH:9]=3)=[CH:26][CH:25]=2)[CH:21]=[CH:22][CH:23]=1

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 463118956-(3-Fluorophenyl)pyridin-3-amineHCID 58447828HCID 58447828、化合物

生成物 1

HCID 58447638HCID 58447638、化合物

試薬・触媒・溶媒 3

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

実験手順

A mixture of 2-(6-thiomorpholinopyridin-3-yl)acetic acid 219-4 (92 mg, 0.39 mmol), 6-(3-fluorophenyl)pyridin-3-amine 219-1 (73 mg, 0.39 mmol), HATU (162 mg, 0.43 mmol) and DIEA (104 μl, 0.6 mmol) in DMF (1.0 ml) was stirred at room temperature overnight. Then it was redistributed between water (30 ml) and ethyl acetate (40 ml). The organic phase was dried over Na2SO4 and concentrated by rotary evaporation. Silica gel column chromatography (with ethyl acetate/hexanes from 1:10 to 2:1 as eluent) gave N-(6-(3-fluorophenyl)pyridin-3-yl)-2-(6-thiomorpholinopyridin-3-yl)acetamide 219-5 as solid. Step 7. N-(6-(3-fluorophenyl)pyridin-3-yl)-2-(6-thiomorpholinopyridin-3-yl)acetamide 219-5 (114 mg, 0.28 mmol) was treated with mCPBA in DCM (2 ml) at 0° C. The mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate (30 mL), washed with 5% Na2CO3 solution, dried over Na2SO4 and concentrated by rotary evaporation. The residue was subjected to reverse phase HPLC purification and gave N-(6-(3-fluorophenyl)pyridin-3-yl)-2-(S,S-dioxo-6-thiomorpholinopyridin-3-yl)acetamide 219 as solid. MS m/z 396.3 (M+1); 1H NMR 400 MHz (DMSO-d6) δ 10.53 (s, 1 H), 8.82 (d, 1 H), 8.16 (dd, 1 H), 8.11 (d, 1 H), 7.99 (d, 1 H), 7.92-7.80 (m, 2 H), 7.60 (dd, 1 H), 7.50 (m, 1 H), 7.22 (m, 1 H), 7.02 (d, 1 H), 4.06-4.01 (m, 4 H), 3.61 (s, 2 H), 3.10-3.05 (m, 4 H).

後処理

  1. dry with materialThe organic phase was dried over Na2SO4
  2. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-412f3af16dcd47cf95fb06968c04cd2f
出典データセット
uspto-grants-2016_01
特許番号
US09238646B2

反応ノート

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