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Chloroacetaldehyde → 6-(2-Chloroethyl)-2-[3-(4-chlorophenyl)ureido]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide

HRID 1483203
ノート
印刷プレビュー

反応式

HRID 1483203 の反応式
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:30])[NH:17][C:18]2[S:26][C:21]3[CH2:22][NH:23][CH2:24][CH2:25][C:20]=3[C:19]=2[C:27]([NH2:29])=[O:28])=[CH:11][CH:10]=1.S([O-])([O-])(=O)=O.[Mg+2].[Cl:37][CH2:38][CH:39]=O.C([BH3-])#N.[Na+]>CO.O1CCCC1.C(O)(=O)C.C(=O)(O)[O-].[Na+]>[Cl:37][CH2:38][CH2:39][N:23]1[CH2:24][CH2:25][C:20]2[C:19]([C:27]([NH2:29])=[O:28])=[C:18]([NH:17][C:16]([NH:15][C:12]3[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][CH:13]=3)=[O:30])[S:26][C:21]=2[CH2:22]1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 33ChloroacetaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5003444Sodium cyanoborohydrideHCID 1182698802-[3-(4-Chlorophenyl)ureido]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide trifluoroacetate

生成物 1

HCID 1182698736-(2-Chloroethyl)-2-[3-(4-chlorophenyl)ureido]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide収率 99%

試薬・触媒・溶媒 4

HCID 176Acetic Acid触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a slurry of compound A4 (200 mg, 0.431 mmol) and magnesium sulfate (2 g) in methanol (4 mL) and tetrahydrofuran (2 mL) was added two drops of glacial acetic acid and 2-chloroacetaldehyde (45% in water, 0.340 mL, 1.95 mmol). After stirring at room temperature for 5 min, sodium cyanoborohydride (271 mg, 4.31 mmol) was added and the reaction mixture was stirred for an additional 16 h at room temperature. After this time, the reaction was diluted with saturated aqueous sodium bicarbonate (100 mL), sonicated, and filtered. The filter cake was washed with water (50 mL) and triturated with methylene chloride to afford compound B1 as a white solid (176 mg, 99%): 1H NMR (300 MHz, DMSO-d6) δ 10.94 (s, 1H), 10.19 (s, 1H), 7.57-7.29 (m, 5H), 6.87 (bs, 1H), 3.76 (t, J=6.6 Hz, 2H), 3.57 (s, 2H), 2.87-2.71 (m, 6H). MS (M+H) 413.

後処理

  1. stirringthe reaction mixture was stirred for an additional 16 h at room temperature
  2. customsonicated
  3. filtrationfiltered
  4. washThe filter cake was washed with water (50 mL)
  5. customtriturated with methylene chloride

出典と根拠

ORDレコード
ord-5dfb5ac97b6f4a21bdded7217f88a4bf
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09416141B2

反応ノート

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