Diisopropylethylamine → N-[(S)-1-(1-Cyanocyclopropylcarbamoyl)-3,3-difluoro-4-phenylbutyl]-8-azaspiro[4.5]decane-8-carboxamide

HRID 1664720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1664720
CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:35][C:36]1([C:39]#[N:40])[CH2:38][CH2:37]1.[CH2:41]1[C:45]2([CH2:50][CH2:49][N:48]([C:51]([NH:53][C@@H:54]([CH2:58][C:59]([F:68])([F:67])[CH2:60][C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[C:55](O)=[O:56])=[O:52])[CH2:47][CH2:46]2)[CH2:44][CH2:43][CH2:42]1>CN(C=O)C>[C:39]([C:36]1([NH:35][C:55]([C@@H:54]([NH:53][C:51]([N:48]2[CH2:47][CH2:46][C:45]3([CH2:44][CH2:43][CH2:42][CH2:41]3)[CH2:50][CH2:49]2)=[O:52])[CH2:58][C:59]([F:67])([F:68])[CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)=[O:56])[CH2:38][CH2:37]1)#[N:40]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 66661164(S)-2-[(8-Azaspiro[4.5]decane-8-carbonyl)amino]-4,4-difluoro-5-phenylpentanoic acid

Produkt 1

HCID 24996348N-[(S)-1-(1-Cyanocyclopropylcarbamoyl)-3,3-difluoro-4-phenylbutyl]-8-azaspiro[4.5]decane-8-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (331 μl, 252 mg, 1.95 mmol, 4 eq.), HATU (185 mg, 0.49 mmol, 1 eq.) and 1-aminocyclopropanecarbonitrile hydrochloride (58 mg, 0.49 mmol, 1 eq.) were added successively to a solution of the (S)-2-[(8-azaspiro[4.5]decane-8-carbonyl)amino]-4,4-difluoro-5-phenylpentanoic acid obtained as a crude product (192 mg, 0.49 mmol) in 10 ml of DMF. The reaction mixture was stirred at RT overnight and, the next day, concentrated under reduced pressure. The residue thus obtained was purified by preparative HPLC (gradient: acetonitrile/water and addition of 0.05% TFA). The title compound was obtained in the form of a colorless crystalline material.

Aufarbeitung

  1. concentrationthe next day, concentrated under reduced pressure
  2. customThe residue thus obtained
  3. customwas purified by preparative HPLC (gradient: acetonitrile/water and addition of 0.05% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-de68fad26a344dddb9e252b21ebdf6af
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039480B2

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