Diisopropylethylamine → HCID 136335775, compound

HRID 1431964Notes

Reaction equation

HRID 1431964 reaction equation
Cl.Cl.[Br:3][C:4]1[CH:5]=[C:6]([CH:24]=[C:25]([Br:27])[CH:26]=1)[CH2:7][O:8][C@@H:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C@H:10]1[N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(N(C(C)C)CC)(C)C.Cl[CH2:38][C:39]1[NH:40][C:41](=[O:44])[NH:42][N:43]=1>CN(C)C=O.ClCCl>[Br:3][C:4]1[CH:5]=[C:6]([CH:24]=[C:25]([Br:27])[CH:26]=1)[CH2:7][O:8][C@@H:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C@H:10]1[N:18]1[CH2:23][CH2:22][N:21]([CH2:38][C:39]2[NH:40][C:41](=[O:44])[NH:42][N:43]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 68920361HCID 68920361, compoundHCID 1355466853H-1,2,4-Triazol-3-one, 5-(chloromethyl)-1,2-dihydro-

Product 1

HCID 136335775HCID 136335775, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

After reconversion to the base, the compound obtained in Step C of Example 1 (2.14 mmol) is dissolved in 30 ml of dimethylformamide. There are added 0.75 ml (4.28 mmol) of diisopropylethylamine and 314 mg (2.35 mmol) of 5-(chloromethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one prepared according to the method described in Tetrahedron Letters, 2000, 41, 8661. The mixture is stirred for 12 hours at ambient temperature and then evaporated to dryness. The residue obtained is taken up in dichloromethane, washed, dried, filtered and evaporated. The oil obtained is purified by flash chromatography on silica to yield the expected product.

Workup

  1. customprepared
  2. customevaporated to dryness
  3. customThe residue obtained
  4. washwashed
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe oil obtained
  9. customis purified by flash chromatography on silica

Sources & evidence

ORD record
ord-2c87197585444fc8a864d8e4bfcdd314
Source dataset
uspto-grants-2009_11
Patent number
US07612061B2

Reaction notes

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