Diisopropylethylamine → HCID 71526312, compound

HRID 1477811Notes

Reaction equation

HRID 1477811 reaction equation
[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([C:15]([OH:17])=O)=[N:8][C:9]=2[O:10][CH2:11][CH:12]2[CH2:14][CH2:13]2)[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[NH2:27][C:28]([CH3:34])([CH3:33])[CH2:29][CH2:30][CH2:31][OH:32]>CN(C=O)C>[OH:32][CH2:31][CH2:30][CH2:29][C:28]([NH:27][C:15]([C:7]1[CH:6]=[N:5][C:4]([CH:1]2[CH2:2][CH2:3]2)=[C:9]([O:10][CH2:11][CH:12]2[CH2:13][CH2:14]2)[N:8]=1)=[O:17])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 131076824-Amino-4-methylpentan-1-olHCID 866823315-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid

Product 1

HCID 71526312HCID 71526312, compoundYield 70.26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid (Example 10 g, 100 mg, 0.43 mmol) was suspended in DMF (3 mL). Mukaiyama Reagent (CAN 878-23-9, 233.8 mg, 0.85 mmol), DIEA (0.31 mL, 2.24 mmol) and 4-amino-4-methyl-pentan-1-ol (CAN 85054-53-1, 101.33 mg, 0.64 mmol) were added and the reaction mixture was stirred at room temperature for 12 hours. The mixture was extracted with ethyl acetate and water; the organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by reverse phase preparative HPLC (Xterra-RP18, 10 μ, 19×250 mm/acetonitrile/10 mM ammonium acetate in water) to give the desired product (100 mg, 70.26%) as colorless sticky liquid; LC-MS (UV peak area, ESI) 96.12%, 334.0 (M+H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate and water
  2. dry with materialthe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by reverse phase preparative HPLC (Xterra-RP18, 10 μ, 19×250 mm/acetonitrile/10 mM ammonium acetate in water)

Sources & evidence

ORD record
ord-6d4412f35f844d769740850cd2d9fbcd
Source dataset
uspto-grants-2016_08
Patent number
US09403808B2

Reaction notes

Loading…