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Dimethylformamide → (S)-N-(7-bromo-3-(neopentyloxy)-2',6'-dihydrospiro[chromeno[2,3-c]pyridine-5,3'-[1,4]oxazine]-5'-yl)formamide

HRID 455664
ノート
印刷プレビュー

反応式

HRID 455664 の反応式
[CH2:1]([OH:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:7][N:8]([CH:10]=[O:11])C.[H-].[Na+].[Br:14][C:15]1[CH:16]=[C:17]2[C@:28]3([N:33]=C(N)[CH2:31][O:30][CH2:29]3)[C:27]3[CH:26]=[C:25](Cl)[N:24]=[CH:23][C:22]=3[O:21][C:18]2=[CH:19][CH:20]=1>C(OCC)(=O)C.O.[Cl-].[Na+].O>[Br:14][C:15]1[CH:16]=[C:17]2[C@:28]3([N:33]=[C:7]([NH:8][CH:10]=[O:11])[CH2:31][O:30][CH2:29]3)[C:27]3[CH:26]=[C:25]([O:6][CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])[N:24]=[CH:23][C:22]=3[O:21][C:18]2=[CH:19][CH:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 6404Neopentyl alcoholHCID 24758Sodium hydrideHCID 58465879(S)-7-bromo-3-chloro-2',6'-dihydrospiro[chromeno [2,3-c]pyridine-5,3'-[1,4]oxazin]-5'-amine

生成物 1

HCID 86658384(S)-N-(7-bromo-3-(neopentyloxy)-2',6'-dihydrospiro[chromeno[2,3-c]pyridine-5,3'-[1,4]oxazine]-5'-yl)formamide

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 8857Ethyl Acetate溶媒
HCID 57417360Sodium chloride; water溶媒

実験手順

A vial was charged with neopentyl alcohol (0.579 g, 6.57 mmol) and DMF (6.57 mL). Sodium hydride (60% in mineral oil; 0.263 g, 6.57 mmol) was added and the reaction was stirred for 10 minutes at room temperature. The vial was heated to 100° C. for 5 min. The vial was cooled to rt. (S)-7-bromo-3-chloro-2′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,3′-[1,4]oxazin]-5′-amine (0.500 g, 1.314 mmol) was added in one portion. The vial was sealed and heated to 100° C. three hours. The mixture was diluted with ethyl acetate and water. A small amount of brine was added and the layers were separated. The aq. layer was extracted twice with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography (0-100% EtOAc/Hexanes) to give 175 mg of (S)—N-(7-bromo-3-(neopentyloxy)-2′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,3′-[1,4]oxazine]-5′-yl)formamide as a light yellow solid.

後処理

  1. temperatureThe vial was heated to 100° C. for 5 min
  2. temperatureThe vial was cooled to rt
  3. customThe vial was sealed
  4. temperatureheated to 100° C. three hours
  5. customthe layers were separated
  6. extractionThe aq. layer was extracted twice with ethyl acetate
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography (0-100% EtOAc/Hexanes)

出典と根拠

ORDレコード
ord-8dcd9304798f489cab057b8651d8bf7c
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08497264B2

反応ノート

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