Diisopropylethylamine → HCID 71525485, compound

HRID 1477770Notes

Reaction equation

HRID 1477770 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([C:15]2[N:20]=[C:19]([C:21]([OH:23])=O)[CH:18]=[N:17][C:16]=2[CH:24]2[CH2:26][CH2:25]2)[CH:12]=[CH:13][CH:14]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[CH3:59][C:60]([CH3:67])([C:62]1[S:63][CH:64]=[CH:65][N:66]=1)[NH2:61]>CN(C=O)C>[CH3:59][C:60]([NH:61][C:21]([C:19]1[CH:18]=[N:17][C:16]([CH:24]2[CH2:26][CH2:25]2)=[C:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([Cl:8])[CH:10]=2)[N:20]=1)=[O:23])([C:62]1[S:63][CH:64]=[CH:65][N:66]=1)[CH3:67]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86682319HCID 86682319, compoundHCID 86682320HCID 86682320, compound

Product 1

HCID 71525485HCID 71525485, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(3-Chloro-phenyl)-5-cyclopropyl-pyrazine-2-carboxylic acid triethylamine salt (1:1) (Example 3a, 0.077 g, 205 μmol) was suspended in DMF (770 μL). TBTU (78.9 mg, 246 mmol), DIEA (106 mg, 136 μl) and α,α-dimethyl-2-thiazolemethanamine hydrochloride (43.9 mg, 246 μmol) were added and the reaction mixture was stirred at room temperature for 2 hours. The mixture was extracted with ethyl acetate and water; the organic phase was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 10 g, 5% to 50% ethyl acetate in n-heptane) to give the desired product (48 mg, 59%) as white solid; LC-MS (UV peak area, ESI) 94%, 399.1042 (M+H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate and water
  2. dry with materialthe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography (silica gel, 10 g, 5% to 50% ethyl acetate in n-heptane)

Sources & evidence

ORD record
ord-3cf39f0542544ddaa5918da33ef22443
Source dataset
uspto-grants-2016_08
Patent number
US09403808B2

Reaction notes

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