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Dimethylformamide → HCID 178464157, Verbindung

HRID 1919183
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1919183
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]([N:27]([CH2:38][CH3:39])[C@H:28]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:29](O)=[O:30])[CH3:26].[CH3:40][CH2:41][N:42]([CH:46]([CH3:48])C)[CH:43]([CH3:45])[CH3:44].[NH:49]1[CH2:53][CH2:52][CH2:51][C@H:50]1[C:54]1[NH:55][CH:56]=[C:57](/[CH:59]=[CH:60]/[C:61]2[CH:66]=[CH:65][C:64](/[CH:67]=[CH:68]/[C:69]3[NH:73][C:72]([C@@H:74]4[CH2:78][CH2:77][CH2:76][NH:75]4)=[N:71][CH:70]=3)=[CH:63][CH:62]=2)[N:58]=1.CN(C=[O:83])C>>[CH2:46]([N:42]([CH2:41][CH3:40])[C@H:43]([C:44]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:45]([N:75]1[CH2:76][CH2:77][CH2:78][C@H:74]1[C:72]1[NH:73][C:69](/[CH:68]=[CH:67]/[C:64]2[CH:63]=[CH:62][C:61](/[CH:60]=[CH:59]/[C:57]3[N:58]=[C:54]([C@@H:50]4[CH2:51][CH2:52][CH2:53][N:49]4[C:29](=[O:30])[C@@H:28]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:27]([CH2:38][CH3:39])[CH2:25][CH3:26])[NH:55][CH:56]=3)=[CH:66][CH:65]=2)=[CH:70][N:71]=1)=[O:83])[CH3:48]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 6228Dimethylformamide2×HCID 81531DiisopropylethylamineHCID 1091378(R)-2-(diethylamino)-2-phenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178437181HCID 178437181, Verbindung

Produkt 1

HCID 178464157
HCID 178464157, Verbindung

Versuchsvorschrift

HATU (76 mg, 0.20 mmol) was added to a stirred solution of (R)-2-(diethylamino)-2-phenylacetic acid (49 mg, 0.20 mmol) in DMF (1 mL) and DIPEA (0.14 mL, 0.80 mmole) and the mixture was stirred for 5 minutes. Then a solution of 1-((E)-2-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-4-yl)vinyl)-4-((E)-2-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)vinyl)benzene (40 mg, 0.10 mmol) in DMF (1 mL) was added and the resulting solution was stirred under argon for 16 hrs. The reaction mixture was purified directly by HPLC and the resulting TFA salt of the desired product was absorbed onto an SCX ion-exchange cartridge with methanol and liberated with a solution of 2 M NH3 in methanol. The fractions containing the desired product were concentrated to yield (1R)-2-((2S)-2-(4-((E)-2-(4-((E)-2-(2-((2S)-1-((2R)-2-(diethylamino)-2-phenylacetyl)-2-pyrrolidinyl)-1H-imidazol-5-yl)vinyl)phenyl)vinyl)-1H-imidazol-2-yl)-1-pyrrolidinyl)-N,N-diethyl-2-oxo-1-phenylethanamine (35.8 mg) as a pale yellow solid.

Aufarbeitung

  1. stirringthe resulting solution was stirred under argon for 16 hrs
  2. customThe reaction mixture was purified directly by HPLC
  3. customthe resulting TFA salt of the desired product was absorbed onto an SCX ion-exchange cartridge with methanol
  4. additionThe fractions containing the desired product
  5. concentrationwere concentrated

Quellen und Nachweise

ORD-Eintrag
ord-ebd791ab52c14c87a2d1a18d6305befd
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08618153B2

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