Hydrochloric Acid → 7-[[(7S)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxylic acid

HRID 2364758ノート

反応式

HRID 2364758 の反応式
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[C@H:6]([CH2:14][CH3:15])[N:5]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:4]=2[N:3]=1.[NH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:31]([O:33]C)=[O:32])=[C:26]2[C:30]=1[O:29][CH2:28][CH2:27]2.Cl>C(O)C.O>[CH:16]1([N:5]2[C:4]3[N:3]=[C:2]([NH:21][C:22]4[CH:23]=[CH:24][C:25]([C:31]([OH:33])=[O:32])=[C:26]5[C:30]=4[O:29][CH2:28][CH2:27]5)[N:11]=[CH:10][C:9]=3[N:8]([CH3:12])[C:7](=[O:13])[C@@H:6]2[CH2:14][CH3:15])[CH2:20][CH2:19][CH2:18][CH2:17]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 68107686Methyl 7-amino-2,3-dihydrobenzofuran-4-carboxylateHCID 86668257(7S)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-7H-pteridin-6-one

生成物 1

HCID 681076557-[[(7S)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxylic acid収率 62%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

(7S)-2-Chloro-8-cyclopentyl-7-ethyl-5-methyl-7H-pteridin-6-one 41f (300 mg, 1.70 mmol) and methyl 7-amino-2,3-dihydrobenzofuran-4-carboxylate 1g (543 mg, 1.80 mmol) were dissolved in 34 mL of the mixture solvent of ethanol and water (V/V=1:2.4) followed by the addition of 0.4 mL of concentrated hydrochloric acid and heated to reflux for 16 hours. The reaction solution was cooled down to room temperature, put into the refrigerator for 1 hour and filtered. The filter cake was washed with water (50 mL) and dissolved in 20 mL of the mixture solvent of water and 1 M lithium hydroxide (V/V=1:1), extracted with ethyl acetate (50 mL×2), the aqueous phase was added dropwise with 1 M hydrochloric acid to adjust pH to 2 resulting in the formation of precipitate. The precipitate was filtered to obtain the title compound 7-[[(7S)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxylic acid 41g (0.45 g, yield: 62.0%) as a white solid.

後処理

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. filtrationfiltered
  4. washThe filter cake was washed with water (50 mL)
  5. dissolutiondissolved in 20 mL of the mixture solvent of water and 1 M lithium hydroxide (V/V=1:1)
  6. extractionextracted with ethyl acetate (50 mL×2)
  7. additionthe aqueous phase was added dropwise with 1 M hydrochloric acid
  8. filtrationThe precipitate was filtered

出典と根拠

ORDレコード
ord-af11ed7077bb4f48a0f834ba95815168
出典データセット
uspto-grants-2014_04
特許番号
US08691822B2

反応ノート

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