Diisopropylethylamine → HCID 58447638, 화합물

HRID 592254노트

반응식

HRID 592254 반응식
[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

참가 물질

8

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 463118956-(3-Fluorophenyl)pyridin-3-amineHCID 58447828HCID 58447828, 화합물

생성물 1

HCID 58447638HCID 58447638, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-412f3af16dcd47cf95fb06968c04cd2f
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238646B2

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