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Formaldehyde → N-{4-(4-bromo-2-fluoro-phenylamino)-7-[2-(2-dimethylamino-propionylamino)-ethoxy]-quinazolin-6-yl}-acrylamide

HRID 81455
ノート
印刷プレビュー

反応式

HRID 81455 の反応式
N[CH:2]([CH3:33])[C:3]([NH:5][CH2:6][CH2:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=3[F:27])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[NH:28][C:29](=[O:32])[CH:30]=[CH2:31])=[O:4].[CH2:34]=O.[C:36]([BH3-])#[N:37].[Na+]>C1COCC1.CO>[Br:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:13]2[C:12]3[C:17](=[CH:18][C:9]([O:8][CH2:7][CH2:6][NH:5][C:3](=[O:4])[CH:2]([N:37]([CH3:36])[CH3:34])[CH3:33])=[C:10]([NH:28][C:29](=[O:32])[CH:30]=[CH2:31])[CH:11]=3)[N:16]=[CH:15][N:14]=2)=[C:21]([F:27])[CH:22]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 16678543N-[7-[2-(2-amino-propionylamino)-ethoxy]-4-(4-bromo-2-fluoro-phenylamino)-quinazolin-6-yl]-acrylamide

生成物 1

HCID 16679451N-{4-(4-bromo-2-fluoro-phenylamino)-7-[2-(2-dimethylamino-propionylamino)-ethoxy]-quinazolin-6-yl}-acrylamide収率 73%

試薬・触媒・溶媒 2

HCID 887
Methanol
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

N-[7-[2-(2-amino-propionylamino)-ethoxy]-4-(4-bromo-2-fluoro-phenylamino)-quinazolin-6-yl]-acrylamide (30 mg, 0.06 mmol) and 37 weight % of formaldehyde (9 μl, 0.12 mmol) were diluted with THF (1 ml) and methanol (1 ml), and stirred at room temperature for 10 min. Sodium cyanoborohydride (11 mg, 0.17 mmol) was added thereto, and the solution was stirred for 4 hours. The resulting solution was distilled under a reduced pressure to remove the solvent, saturated sodium bicarbonate aqueous solution (20 ml) was added thereto, and extracted with chloroform (20 ml) twice. The separated organic layer was dried over magnesium sulfate, filtered and distilled under a reduced pressure, and resulting impure residue was subjected to column chromatography to obtain the title compound 23 mg (yield: 73%).

後処理

  1. stirringthe solution was stirred for 4 hours
  2. distillationThe resulting solution was distilled under a reduced pressure
  3. customto remove the solvent, saturated sodium bicarbonate aqueous solution (20 ml)
  4. additionwas added
  5. extractionextracted with chloroform (20 ml) twice
  6. dry with materialThe separated organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. distillationdistilled under a reduced pressure
  9. customresulting impure residue

出典と根拠

ORDレコード
ord-997f1c4d2fe946ed96883f8c9eb2b539
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846699B2

反応ノート

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