Diisopropylethylamine → 5-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid ((S)-carbamoyl-phenyl-methyl)-amide

HRID 1477779

Reaktionsgleichung

Reaktionsgleichung von HRID 1477779
[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.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:49][C@@H:50]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:51]([NH2:53])=[O:52]>CN(C=O)C>[C:51]([C@@H:50]([NH:49][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])[C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)(=[O:52])[NH2:53]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 729986(S)-(+)-2-Phenylglycine amideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 866823315-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid

Produkt 1

HCID 715255765-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid ((S)-carbamoyl-phenyl-methyl)-amideAusbeute 9,58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid (Example 10 g, 100 mg, 0.43 mmol) was suspended in DMF (3 mL). TBTU (224.14 mg, 0.85 mmol), DIEA (0.31 mL, 2.24 mmol) and (αS)-α-amino-benzeneacetamide (CAN 6485-52-5, 51.2 mg, 0.51 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 (Xbridge-C18, 5 μ, 19×250 mm/acetonitrile/0.1% ammonia in water) to give the desired product (15 mg, 9.58%) as white solid; LC-MS (UV peak area, ESI) 93.20%, 367.4 (M+H).

Aufarbeitung

  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 (Xbridge-C18, 5 μ, 19×250 mm/acetonitrile/0.1% ammonia in water)

Quellen und Nachweise

ORD-Eintrag
ord-45669c99ab514df781379e6c3717cfaa
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403808B2

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