Sulfur, trifluoro(N-methylmethanaminato)- → 9-(1-fluoro-2-morpholinoethyl)-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

HRID 707483

反応式

HRID 707483 の反応式
CN(S(F)(F)[F:5])C.O[CH:9]([C:17]1[CH:26]=[N:25][C:24]2[N:23]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[C:22](=[O:36])[N:21]3[N:37]=[CH:38][N:39]=[C:20]3[C:19]=2[CH:18]=1)[CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>C(#N)C.C(=O)(O)[O-].[Na+]>[F:5][CH:9]([C:17]1[CH:26]=[N:25][C:24]2[N:23]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[C:22](=[O:36])[N:21]3[N:37]=[CH:38][N:39]=[C:20]3[C:19]=2[CH:18]=1)[CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

参加物

5

反応物 2

HCID 123203Sulfur, trifluoro(N-methylmethanaminato)-2 回HCID 727063249-(1-hydroxy-2-morpholinoethyl)-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

生成物 1

HCID 867053969-(1-fluoro-2-morpholinoethyl)-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one収率 22.8%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
60 °C

実験手順

(Dimethylamino)sulfur trifluoride (0.010 ml, 0.18 mmol) was added to a stirred solution of 9-(1-hydroxy-2-morpholinoethyl)-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (49 mg, 0.090 mmol) in acetonitrile (1 ml). After 4 hours, additional (dimethylamino)sulfur trifluoride (0.035 ml, 0.36 mmol) was added and the mixture was stirred at 60° C. for 20 hours, cooled to room temperature, diluted with aqueous sodium bicarbonate (3 mL) and extracted with DCM (2×3 mL). The combined extracts were concentrated under a stream of nitrogen and the residue was taken up in methanol, filtered and purified by preparative HPLC. The resulting material retained some impurities so it was diluted with aqueous sodium bicarbonate (3 mL) and extracted with DCM (2×3 mL). The combined extracts were concentrated under a stream of nitrogen and the residue was purified by flash chromatography (elution with 0-40% IPA in ethyl acetate) to afford 9 mg (21%) of 269 as a white powder.

後処理

  1. temperaturecooled to room temperature
  2. extractionextracted with DCM (2×3 mL)
  3. concentrationThe combined extracts were concentrated under a stream of nitrogen
  4. filtrationfiltered
  5. custompurified by preparative HPLC
  6. additionwas diluted with aqueous sodium bicarbonate (3 mL)
  7. extractionextracted with DCM (2×3 mL)
  8. concentrationThe combined extracts were concentrated under a stream of nitrogen
  9. customthe residue was purified by flash chromatography (elution with 0-40% IPA in ethyl acetate)

出典と根拠

ORDレコード
ord-ab221ffb96ac49afa79b31d73c725821
出典データセット
uspto-grants-2015_11
特許番号
US09175010B2

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