3-Fluorobenzyl isocyanate → HCID 58055089、化合物

HRID 1685082ノート

反応式

HRID 1685082 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[CH2:5][N:6]=[C:7]=[O:8].[Cl:12][CH2:13][C:14]1[N:18]=[C:17]([NH2:19])[S:16][N:15]=1>CN(C1C=CN=CC=1)C.CN1C(=O)CCC1.CCOC(C)=O>[Cl:12][CH2:13][C:14]1[N:18]=[C:17]([NH:19][C:7]([NH:6][CH2:5][C:4]2[CH:9]=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)=[O:8])[S:16][N:15]=1

参加物

6

反応物 2

HCID 6434993-Fluorobenzyl isocyanateHCID 140126043-(Chloromethyl)-1,2,4-thiadiazol-5-amine2 回

生成物 1

HCID 58055089HCID 58055089、化合物収率 72%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

3-Fluorobenzyl isocyanate (1.3 g, 8 mmol) was added into a mixture of Intermediate 38: 3-chloromethyl-[1,2,4]thiadiazol-5-ylamine (0.83 g, 5.5 mmol), and DMAP (22 mg, 0.14 mmol) in NMP (11 mL). The reaction mixture was heated in a microwave reactor for 1 hour at 100 C and then cooled to ambient temperature. The reaction mixture was diluted with EtOAc (75 mL) and washed with water (30 mL×2). The aqueous phase was extracted with EtOAc (40 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to give the crude product, which was purified by silica gel column chromatography to afford 1-(3-chloromethyl-[1,2,4]thiadiazol-5-yl)-3-(3-fluoro-benzyl)-urea as an off-white solid (1.2 g, 72%). LC-MS (m/z): 303.0 (M+H)

後処理

  1. temperatureThe reaction mixture was heated in a microwave reactor for 1 hour at 100 C
  2. washwashed with water (30 mL×2)
  3. extractionThe aqueous phase was extracted with EtOAc (40 mL×2)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give the crude product, which
  9. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-1b0d1ed5707f46eaa4a379af29dfcaf6
出典データセット
uspto-grants-2012_04
特許番号
US08148380B2

反応ノート

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