Ammonia → 1-[4-((1S,2S)-2-{[(2R)-2-methylpyrrolidin-1-yl]methyl}cyclopropyl)phenyl]pyrrolidin-2-one

HRID 73315

Reaction equation

HRID 73315 reaction equation
N1[NH:2][C:3](=[O:7])[CH:4]=[CH:5][CH:6]=1.Br[C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:17][C@@H:16]2[CH2:18][N:19]2[CH2:23][CH2:22][CH2:21][C@H:20]2[CH3:24])=[CH:11][CH:10]=1.N>>[CH3:24][C@@H:20]1[CH2:21][CH2:22][CH2:23][N:19]1[CH2:18][C@H:16]1[CH2:17][C@@H:15]1[C:12]1[CH:13]=[CH:14][C:9]([N:2]2[CH2:6][CH2:5][CH2:4][C:3]2=[O:7])=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 681533(2H)-PyridazinoneHCID 66796087(R)-1-(((1S,2S)-2-(4-bromophenyl)cyclopropyl)methyl)-2-methylpyrrolidine

Product 1

HCID 441992601-[4-((1S,2S)-2-{[(2R)-2-methylpyrrolidin-1-yl]methyl}cyclopropyl)phenyl]pyrrolidin-2-one

Procedure

The title compound was prepared using the procedure described in Example 35B substituting pyrrolidin-2-one for pyridazin-3(2H)-one and substituting the product from Example 35A for the product from Example 34F. 1H NMR (300 MHz, CD3OD) δ 0.89-0.96 (m, 1H), 1.01-0.08 (m, 1H), 1.22 (d, J=6 Hz, 3H), 1.25-1.30 (m, 1H), 1.48-1.55 (m, 1H), 1.8-1.89 (m, 4H), 2.03-2.27 (m, 4H), 2.57 (t, J=6 Hz, 2H), 2.65-2.74 (m, 1H), 3.22 (q, J=6 Hz, 1H), 3.33-3.40 (m, 1H), 3.89 (t, J=6 Hz, 2H), 7.10 (d, J=9 Hz, 2H), 7.46 (d, J=9 Hz, 2H). MS (DCl—NH3) m/z 299 (M+H)+.

Sources & evidence

ORD record
ord-ff3ae7bcbe6e475d929323ba5b739d05
Source dataset
uspto-grants-2014_09
Patent number
US08829041B2

Linked notes

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