1-(Bromomethyl)-2-(trifluoromethyl)benzene → HCID 59383146, compound

HRID 555696Notes

Reaction equation

HRID 555696 reaction equation
[C:1]([C:4]12[CH2:11][CH2:10][C:7]([NH:12][CH2:13][C:14]([N:16]3[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]3[C:22]#[N:23])=[O:15])([CH2:8][CH2:9]1)[CH2:6][CH2:5]2)([OH:3])=[O:2].[F:24][C:25]([F:35])([F:34])[C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH2:28]Br>>[F:21][C@@H:19]1[CH2:20][N:16]([C:14](=[O:15])[CH2:13][NH:12][C:7]23[CH2:10][CH2:11][C:4]([C:1]([O:3][CH2:28][C:27]4[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=4[C:25]([F:24])([F:34])[F:35])=[O:2])([CH2:9][CH2:8]2)[CH2:5][CH2:6]3)[C@H:17]([C:22]#[N:23])[CH2:18]1

Participants

3

Reactant 2

HCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Product 1

HCID 59383146HCID 59383146, compoundYield 89.3%

Procedure

In a similar manner to Example 8, (2S,4S)-1-[[N-(4-carboxybicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (30.0 mg) and 2-trifluoromethylbenzyl bromide (25.4 mg) were used to obtain (2S,4S)-4-fluoro-1-[[N-[4-(2-trifluoromethylbenzyl)oxycarbonyl bicyclo[2.2.2]oct-1-yl]amino]acetyl]pyrrolidine-2-carbonitrile (39.9 mg).

Sources & evidence

ORD record
ord-448c0fc17b594d6cb67311e2dce0374d
Source dataset
uspto-grants-2011_11
Patent number
US08053465B2

Reaction notes

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