Acetyl chloride → HCID 178473060、化合物

HRID 2173948ノート

反応式

HRID 2173948 の反応式
[C:1]([C:3]1[CH:34]=[CH:33][C:6]2[NH:7][C:8]([C:10]([C:21]3[C:29]([O:30][CH3:31])=[CH:28][C:27]([CH3:32])=[C:26]4[C:22]=3[CH:23]=[CH:24][NH:25]4)([O:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:11]([F:14])([F:13])[F:12])=[N:9][C:5]=2[CH:4]=1)#[N:2].[C:35](Cl)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C>[C:1]([C:3]1[CH:34]=[CH:33][C:6]2[NH:7][C:8]([C:10]([C:21]3[C:29]([O:30][CH3:31])=[CH:28][C:27]([CH3:32])=[C:26]4[C:22]=3[CH:23]=[CH:24][NH:25]4)([O:15][CH2:16][C:17]([O:19][CH2:20][CH3:35])=[O:18])[C:11]([F:12])([F:13])[F:14])=[N:9][C:5]=2[CH:4]=1)#[N:2]

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 178501803HCID 178501803、化合物

生成物 1

HCID 178473060HCID 178473060、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

(+) or (−)-Methyl 2-(1-(5-cyano-1H-benzo[d]imidazol-2-yl)-2,2,2-trifluoro-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethoxy)acetate (tr=3.5 min—from Example 35-B) (54 mg, 0.114 mmol) was dissolved in ethanol (2.0 mL). This solution was added to a mixture of acetyl chloride (1.0 mL) in ethanol (20.0 mL) at 0° C. This mixture was gradually warmed to room temperature and stirred for 16 hr. The reaction solution was basified with saturated sodium bicarbonate solution and the majority of the ethanol was removed in vacuo. The resulting reaction mixture was partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. This material was purified using FCC eluting with ethyl acetate/heptane (0-60%) to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.89 (br.s., 1H) 11.09 (br. s., 1H) 8.26 (s, 1H) 7.83-8.06 (m, 1H) 7.49-7.73 (m, 1H) 7.38 (t, J=2.78 Hz, 1H) 6.91-6.96 (m, 1H) 6.74 (s, 1H) 3.98-4.36 (m, 2H) 3.73-3.97 (m, 2H) 3.04-3.06 (s, 3H) 2.47-2.50 (s, 3H) 0.97-1.08 (m, 3H) HRMS calcd. for C24H21F3N4O4 (M+H)+ 487.1548. found 487.1576.

後処理

  1. customthe majority of the ethanol was removed in vacuo
  2. customThe resulting reaction mixture
  3. customwas partitioned between ethyl acetate and water
  4. customThe layers were separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThis material was purified
  10. washeluting with ethyl acetate/heptane (0-60%)

出典と根拠

ORDレコード
ord-74999d1dbccc4f029a3fcc40e32cf266
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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