Potassium Carbonate → 8-(1-cyclopropyl-6-fluoro-1H-benzimidazol-2-yl)-1,6-naphthyridine

HRID 1048947ノート

反応式

HRID 1048947 の反応式
[CH:1]1([NH:4][C:5]2[C:6]([NH2:12])=[CH:7][CH:8]=[C:9]([F:11])[CH:10]=2)[CH2:3][CH2:2]1.[N:13]1[C:22]2[C:17](=[CH:18][N:19]=[CH:20][C:21]=2[CH:23]=O)[CH:16]=[CH:15][CH:14]=1.OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[CH:1]1([N:4]2[C:5]3[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=3[N:12]=[C:23]2[C:21]2[CH:20]=[N:19][CH:18]=[C:17]3[C:22]=2[N:13]=[CH:14][CH:15]=[CH:16]3)[CH2:3][CH2:2]1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 534219291,6-Naphthyridine-8-carbaldehydeHCID 545925541-N-cyclopropyl-5-fluorobenzene-1,2-diamine

生成物 1

HCID 566453598-(1-cyclopropyl-6-fluoro-1H-benzimidazol-2-yl)-1,6-naphthyridine

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of N2-cyclopropyl-4-fluorobenzene-1,2-diamine (0.080 g, 0.48 mmol) in DMF (1.17 mL) and water (0.04 mL) were added the title compound from Example 8 Step A (0.084 g, 0.53 mmol) and OXONE® (0.192 g, 0.313 mmol). The resulting mixture was stirred at room temperature for 1 hour, then diluted with ethyl acetate and water. Solid potassium carbonate was added until the aqueous layer was basic (pH ˜9). Ethyl acetate was added, and the organic layer was separated, washed with water and brine, dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (50% ethyl acetate in hexanes, then 100% ethyl acetate) provided the title compound: LCMS m/z 304.99 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 9.09 (s, 1 H), 9.13 (m, 1 H), 9.07 (s, 1 H), 8.43 (d, J=8.3 Hz, 1 H), 7.78 (dd, J=8.7, 4.8 Hz, 1 H), 7.63 (dd, J=8.2, 4.2 Hz, 1 H), 7.34 (dd, J=8.7, 2.2 Hz, 1 H), 7.07 (m, 1 H), 3.55-3.53 (m, 1 H), 0.62-0.61 (m, 4 H).

後処理

  1. customthe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel (50% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-eca0fbf5738847e48ee478121c018bbf
出典データセット
uspto-grants-2016_07
特許番号
US09382226B2

反応ノート

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