Citric Acid → HCID 57731537、化合物

HRID 2234696ノート

反応式

HRID 2234696 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([NH:29][C:30]4[CH:31]=[N:32][CH:33]=[N:34][CH:35]=4)=[C:22]([CH:28]=3)[C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[CH:16]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1.[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([NH:29][C:30]4[CH:31]=[N:32][CH:33]=[N:34][CH:35]=4)=[C:22]([CH:28]=3)[C:23]([N:25]([CH3:26])[CH3:27])=[O:24])[CH:16]=2)[NH:11][CH:10]=1

参加物

5

反応物 3

HCID 311Citric AcidHCID 14797Potassium HydroxideHCID 57731440HCID 57731440、化合物

生成物 1

HCID 57731537HCID 57731537、化合物収率 43%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

67 mg (0.11 mmol) of 5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-(pyrimidin-5-ylamino)-benzamide was dissolved in 3 mL of hot ethanol. 200 μL of 50% w/v aqueous potassium hydroxide was added and the mixture left at ambient temperature for 4.5 h. 10% w/v aqueous citric acid was added and the mixture partitioned between dichloromethane and water. The aqueous layer was extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and evaporated. The residue was purified by mass-triggered reverse-phase HPLC to afford 21.9 mg (47 μmol, 43%) of 5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-(pyrimidin-5-ylamino)-benzamide as a beige solid. 1H-NMR (500 MHz, d6-DMSO): δ 11.91 (s, br., 1H), 8.64 (s, 1H), 8.55 (d, 1H), 8.51 (s, 2H), 8.17 (d, 1H), 8.12 (s, 1H), 7.74 (d, 1H), 7.73 (dd, 1H), 7.63-7.61 (m, 2H), 7.39 (d, 1H), 7.30 (dd(d), 1H), 7.14 (d, 1H), 7.06 (t, 1H), 3.83 (s, 3H), 2.90 (s, 3H), 2.88 (s, 3H); MS: m/z 465.0 (M+H+).

後処理

  1. additionwas added
  2. additionwas added
  3. customthe mixture partitioned between dichloromethane and water
  4. extractionThe aqueous layer was extracted three times with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by mass-triggered reverse-phase HPLC

出典と根拠

ORDレコード
ord-43fff49cf0c34dfeabebb669591c7855
出典データセット
uspto-grants-2010_05
特許番号
US07709645B2

反応ノート

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