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

HRID 72532Notes

Reaction equation

HRID 72532 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]([F:23])=[CH:19][CH:18]=3)[CH2:12]2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.Cl.[NH2:25][C@H:26]([C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1)[CH3:27]>>[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]([F:23])=[CH:19][CH:18]=3)[CH2:12]2)=[C:6]([CH:10]=1)[C:7]([NH:25][C@H:26]([C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1)[CH3:27])=[O:9]

Participants

3

Reactant 2

HCID 57462942(S)-Methyl 4-(1-aminoethyl)benzoate hydrochlorideHCID 679585065-Chloro-2-(3-(4-fluorophenoxy)pyrrolidin-1-yl)nicotinic acid

Product 1

HCID 67958668methyl 4-((1S)-1-(5-chloro-2-(3-(4-fluorophenoxy)pyrrolidin-1-yl)nicotinamido)ethyl)benzoateYield 40.2%

Procedure

The title compound (D193) (64 mg) was prepared according to the experimental procedure described in Description 146 starting from 5-chloro-2-(3-(4-fluorophenoxy)pyrrolidin-1-yl)nicotinic acid (D138) (110 mg, 0.320 mmol), and (S)-methyl 4-(1-aminoethyl)benzoate (D3) (68.82 mg, 0.320 mmol) MS: (ES/+) m/z: 499.2 [MH+] C26H25ClFN3O4 requires 497.15

Sources & evidence

ORD record
ord-dd7684be12774ab6b9f2d3e32af4ef33
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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