Diisopropylethylamine → HCID 118308169, compound

HRID 1750559Notes

Reaction equation

HRID 1750559 reaction equation
[NH2:1][CH:2]1[CH2:6][C:5]([F:8])([F:7])[CH2:4][CH:3]1[NH:9][S:10]([C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:12])=[O:11].CCN(C(C)C)C(C)C.Cl[C:27]1[CH:32]=[N:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][N:28]=1>CS(C)=O>[F:8][C:5]1([F:7])[CH2:4][CH:3]([NH:9][S:10]([C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:12])=[O:11])[CH:2]([NH:1][C:27]2[CH:32]=[N:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][N:28]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 189876452-Chloro-5-(trifluoromethyl)pyrazineHCID 118308166HCID 118308166, compound

Product 1

HCID 118308169HCID 118308169, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of N-(2-amino-4,4-difluorocyclopentyl)-2-methylpropane-2-sulfonamide (66 mg, 0.26 mmol) in DMSO (650 μl) was added DIPEA (135 μl, 0.77 mmol) and 2-chloro-5-(trifluoromethyl)pyrazine (CAS number 799557-87-2; 47 mg, 0.26 mmol). The reaction mixture was sealed and heated at 120° C. for 18 hours then partitioned between ethyl acetate and water. The organics were washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography (silica, 10-60% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customThe reaction mixture was sealed
  2. customthen partitioned between ethyl acetate and water
  3. washThe organics were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by column chromatography (silica, 10-60% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-f4cdc630d80241a1a6922f5ac5c09481
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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