Ammonia → 4'-{(1S,2S)-2-[(2-Methylpyrrolidin-1-yl)methyl]cyclopropyl}-1,1'-biphenyl-4-carbonitrile

HRID 73290

Reaktionsgleichung

Reaktionsgleichung von HRID 73290
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][C@@H:9]2[CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[CH3:17])=[CH:4][CH:3]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([C@H:25]2C[C@@H]2CN2CCC[C@@H]2C)=[CH:21][CH:20]=1.[NH3:35]>>[CH3:17][CH:13]1[CH2:14][CH2:15][CH2:16][N:12]1[CH2:11][C@H:9]1[CH2:10][C@@H:8]1[C:5]1[CH:6]=[CH:7][C:2]([C:19]2[CH:20]=[CH:21][C:22]([C:25]#[N:35])=[CH:23][CH:24]=2)=[CH:3][CH:4]=1

Komponenten

4

Edukt 3

HCID 222AmmoniaHCID 575153751-{[(1S,2S)-2-(4-bromophenyl)cyclopropyl]methyl}-(2S)-2-methylpyrrolidineHCID 667960881-[2-(4-bromo-phenyl)-(1S,2S)-cyclopropylmethyl]-2-methyl-pyrrolidine

Produkt 1

HCID 441974554'-{(1S,2S)-2-[(2-Methylpyrrolidin-1-yl)methyl]cyclopropyl}-1,1'-biphenyl-4-carbonitrile

Versuchsvorschrift

The title compound was prepared using the procedure described in Example 1E substituting 1-[2-(4-bromo-phenyl)-(1S,2S)-cyclopropylmethyl]-2-methyl-pyrrolidine (the product from Example 5A) for 1-[(1S,2S)-2-(4-bromo-phenyl)-cyclopropylmethyl]-2(S)-methyl-pyrrolidine (the product from Example 1D). 1H NMR (300 MHz, CD3OD) 0.98 (m, 1H), 1.1 (m, 1H), 1.20 (d, J=6 Hz, 2H), 1.34 (m, 1H), 1.49 (m, 1H), 1.84 (m, 3H), 2.06 (m, 2H), 2.51 (m, 1H), 2.61 (m, 1H), 3.06 (dd, J=12 Hz, J=6 Hz, 0.5H), 3.22 (dd, J=12 Hz, J=6 Hz, 0.5H), 3.34 (m, 1H), 7.22 (dd, J=12 Hz, J=6 Hz, 2H), 7.59 (d, J=9 Hz, 2H), 7.77 (s, 4H)<MS (DCl—NH3) m/z 317 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-e3d85132cbe149a8add883456440129f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829041B2

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