3-Fluorobenzyl isocyanate → HCID 58055089, 화합물

HRID 1685082노트

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HRID 1685082 반응식
[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

참가 물질

6

반응물 2

HCID 6434993-Fluorobenzyl isocyanateHCID 140126043-(Chloromethyl)-1,2,4-thiadiazol-5-amine2회

생성물 1

HCID 58055089HCID 58055089, 화합물수율 72%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-1b0d1ed5707f46eaa4a379af29dfcaf6
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148380B2

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