3-Fluorobenzyl isocyanate → HCID 58055089, compound

HRID 1685082Notes

Reaction equation

HRID 1685082 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

HCID 58055089HCID 58055089, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-1b0d1ed5707f46eaa4a379af29dfcaf6
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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