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

HRID 72531Notes

Reaction equation

HRID 72531 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][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)[CH2:12]2)=[C:6]([CH:10]=1)[C:7](O)=[O:8].Cl.[NH2:28][C@H:29]([C:31]1[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=1)[CH3:30]>>[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][CH:20]=[C:19]([C:23]([F:24])([F:26])[F:25])[CH:18]=3)[CH2:12]2)=[C:6]([CH:10]=1)[C:7]([NH:28][C@H:29]([C:31]1[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=1)[CH3:30])=[O:8]

Participants

3

Reactant 2

HCID 57462942(S)-Methyl 4-(1-aminoethyl)benzoate hydrochlorideHCID 679581185-Chloro-2-(3-(3-(trifluoromethyl)phenoxy)pyrrolidin-1-yl)nicotinic acid

Product 1

HCID 67958268methyl 4-((1S)-1-(5-chloro-2-(3-(3-(trifluoromethyl)phenoxy)pyrrolidin-1-yl)nicotinamido)ethyl)benzoateYield 38.3%

Procedure

The title compound (D192) (64 mg) was prepared according to the experimental procedure described in Description 146 starting from 5-chloro-2-(3-(3-(trifluoromethyl)phenoxy)pyrrolidin-1-yl)nicotinic acid (D137) (120 mg, 0.305 mmol) and (S)-methyl 4-(1-aminoethyl)benzoate (D3) (65.7 mg, 0.305 mmol)

Sources & evidence

ORD record
ord-576eadfdf53a4ddc983ef4e8032e0c72
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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