Diisopropylethylamine → HCID 67126448, compound

HRID 2168396Notes

Reaction equation

HRID 2168396 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[C:5]([F:9])=[CH:4][C:3]=1[S:10]([NH2:13])(=[O:12])=[O:11].[O:14]1[CH2:19][CH2:18][CH:17]([CH2:20][NH2:21])[CH2:16][CH2:15]1.C(N(CC)C(C)C)(C)C>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:21][CH2:20][CH:17]2[CH2:18][CH2:19][O:14][CH2:15][CH2:16]2)[C:5]([F:9])=[CH:4][C:3]=1[S:10]([NH2:13])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 27732104-Aminomethyltetrahydropyran2×HCID 27735192-chloro-4,5-difluorobenzenesulfonamide

Product 1

HCID 67126448HCID 67126448, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-4,5-difluorobenzenesulfonamide (0.683 g), (tetrahydro-2H-pyran-4-yl)methanamine (0.346 g), N,N-diisopropylethylamine (0.681 ml) and dioxane (10 ml) were heated at 65° C. for 2.5 days. Additional (tetrahydro-2H-pyran-4-yl)methanamine (0.346 g) and N,N-diisopropylethylamine (0.681 ml) were added and heating was continued at 70° C. for 1.5 days. The reaction mixture was concentrated and column chromatographed on silica gel with 0-3% methanol in dichloromethane as eluent. The obtained solid was triturated with dichloromethane to give the title compound.

Workup

  1. temperatureheating
  2. concentrationThe reaction mixture was concentrated
  3. customcolumn chromatographed on silica gel with 0-3% methanol in dichloromethane as eluent
  4. customThe obtained solid was triturated with dichloromethane

Sources & evidence

ORD record
ord-8df7d2a7a5e6460880f8d125302e2e43
Source dataset
uspto-grants-2015_06
Patent number
US09045420B2

Reaction notes

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