(S)-Methyl 4-(1-aminoethyl)benzoate hydrochloride → methyl 4-((1S)-1-(5-chloro-2-(3-(4-(trifluoromethyl)phenoxy)pyrrolidin-1-yl)nicotinamido)ethyl)benzoate

HRID 72530Notes

Reaction equation

HRID 72530 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:15][CH2:14][CH:13]([O:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[CH2:12]2)=[C:6]([CH:10]=1)[C:7]([O-:9])=O.[Li+].Cl.[NH2:29][C@H:30]([C:32]1[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=1)[CH3:31]>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:15][CH2:14][CH:13]([O:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:25])([F:24])[F:26])=[CH:19][CH:18]=3)[CH2:12]2)=[C:6]([CH:10]=1)[C:7]([NH:29][C@H:30]([C:32]1[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=1)[CH3:31])=[O:9]

Participants

3

Reactant 2

HCID 57462942(S)-Methyl 4-(1-aminoethyl)benzoate hydrochlorideHCID 67958430Lithium 5-chloro-2-(3-(4-(trifluoromethyl)phenoxy)pyrrolidin-1-yl)nicotinate

Product 1

HCID 67958125methyl 4-((1S)-1-(5-chloro-2-(3-(4-(trifluoromethyl)phenoxy)pyrrolidin-1-yl)nicotinamido)ethyl)benzoateYield 27.6%

Procedure

The title compound (D191) (50 mg) was prepared according to the experimental procedure described in Description 148 starting from lithium 5-chloro-2-(3-(4-(trifluoromethyl)phenoxy)pyrrolidin-1-yl)nicotinate (D136) (130 mg, 0.331 mmol) and (S)-methyl 4-(1-aminoethyl)benzoate (D3) (71.19 mg, 0.331 mmol)

Sources & evidence

ORD record
ord-3115c83b775043049fc8645d828efdce
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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