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

HRID 515032

Reaktionsgleichung

Reaktionsgleichung von HRID 515032
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][C@H: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][C@@H: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 66796087(R)-1-(((1S,2S)-2-(4-bromophenyl)cyclopropyl)methyl)-2-methylpyrrolidine2×

Produkt 1

HCID 441991384'-((1S,2S)-2-{[(2R)-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]-(2R)-2-methyl-pyrrolidine (the product from Example 2A) for 1-[(1S,2S)-2-(4-bromo-phenyl)-cyclopropylmethyl]-2(S)-methyl-pyrrolidine (the product from 1D). 1H NMR (300 MHz, CD3OD): δ 0.92(m, 1H), 0.99 (m, 1H), 1.13 (d, J=6 Hz, 2H), 1.24 (m, 1H), 1.43(m, 1H), 1.77(m, 3H), 1.98 (m, 2H), 2.13 (dd, J=12 Hz, J=6 Hz, 1H), 2.30 (q, J=9 Hz, 1H), 2.41 (m, 1H), 2.94 (dd, J=12 Hz, J=6 Hz, 1H), 3.25 (m, 1H), 7.00 (d, J=9 Hz, 2H), 7.36 (d, J=9 Hz, 2H). MS (DCl—NH3) m/z 294 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-6d98723bd53741049762add3fe0bcfe9
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108948B2

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