Diisopropylethylamine → HCID 118308231, compound

HRID 1750579Notes

Reaction equation

HRID 1750579 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[NH:8][C:9](=[O:22])[C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1[N:17]1[N:21]=[CH:20][CH:19]=[N:18]1.Cl[C:24]1[CH:29]=[N:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=1.CCN(C(C)C)C(C)C>CS(C)=O>[CH3:16][C:14]1[CH:13]=[CH:12][C:11]([N:17]2[N:18]=[CH:19][CH:20]=[N:21]2)=[C:10]([CH:15]=1)[C:9]([NH:8][C@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:3]1[NH:2][C:24]1[CH:29]=[N:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=1)=[O:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 189876452-Chloro-5-(trifluoromethyl)pyrazineHCID 118308085HCID 118308085, compound2×

Product 1

HCID 118308231HCID 118308231, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A microwave vial was charged with N-[(1S,2S)-2-aminocyclopentyl]-5-methyl-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride (Intermediate 7; 450 mg, 1.40 mmol), 2-chloro-5-(trifluoromethyl)pyrazine (CAS number 799557-87-2; 306 mg, 1.68 mmol) and DIPEA (733 μl, 4.20 mmol) in dry DMSO (4.7 ml). The reaction was subjected to microwave irradiation at 140° C. for 2 hours and then partitioned between ethyl acetate and water, washed with water, brine and concentrated in vacuo. The crude product was then purified by column chromatography (basic silica, 0-100% ethyl acetate/petrol) to give a cream solid which was then recrystallised from a mixture of ethyl acetate and pentane to afford the title compound.

Workup

  1. customirradiation at 140° C. for 2 hours
  2. custompartitioned between ethyl acetate and water
  3. washwashed with water, brine
  4. concentrationconcentrated in vacuo
  5. customThe crude product was then purified by column chromatography (basic silica, 0-100% ethyl acetate/petrol)
  6. customto give a cream solid which
  7. customwas then recrystallised from a mixture of ethyl acetate and pentane

Sources & evidence

ORD record
ord-f1929b75655e4bc790a2127dbed92d27
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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