6-Chloro-2,4-dimethylnicotinic acid → 4-[(S)-3-(1-{3-[(6-chloro-2,4-dimethyl-pyridine-3-carbonyl)-amino]-1-methyl-propyl}-piperidin-4-yl)-4-methoxymethyl-2-oxo-imidazolidin-1-ylmethyl]-benzoic acid methyl ester

HRID 1711199Notes

Reaction equation

HRID 1711199 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:15][C@@H:14]([CH2:16][O:17][CH3:18])[N:13]([CH:19]3[CH2:24][CH2:23][N:22]([CH:25]([CH3:29])[CH2:26][CH2:27][NH2:28])[CH2:21][CH2:20]3)[C:12]2=[O:30])=[CH:6][CH:5]=1.[Cl:32][C:33]1[CH:41]=[C:40]([CH3:42])[C:36]([C:37](O)=[O:38])=[C:35]([CH3:43])[N:34]=1>>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][N:11]2[CH2:15][C@@H:14]([CH2:16][O:17][CH3:18])[N:13]([CH:19]3[CH2:24][CH2:23][N:22]([CH:25]([CH3:29])[CH2:26][CH2:27][NH:28][C:37]([C:36]4[C:35]([CH3:43])=[N:34][C:33]([Cl:32])=[CH:41][C:40]=4[CH3:42])=[O:38])[CH2:21][CH2:20]3)[C:12]2=[O:30])=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 34465636-Chloro-2,4-dimethylnicotinic acidHCID 687770234-{(S)-3-[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-4-methoxymethyl-2-oxo-imidazolidin-1-ylmethyl}-benzoic acid methyl ester

Product 1

HCID 866295374-[(S)-3-(1-{3-[(6-chloro-2,4-dimethyl-pyridine-3-carbonyl)-amino]-1-methyl-propyl}-piperidin-4-yl)-4-methoxymethyl-2-oxo-imidazolidin-1-ylmethyl]-benzoic acid methyl esterYield 60%

Procedure

According to general procedure E, 4-{(S)-3-[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-4-methoxymethyl-2-oxo-imidazolidin-1-ylmethyl}-benzoic acid methyl ester (40 mg) and 6-chloro-2,4-dimethyl-nicotinic acid gave 4-[(S)-3-(1-{3-[(6-chloro-2,4-dimethyl-pyridine-3-carbonyl)-amino]-1-methyl-propyl}-piperidin-4-yl)-4-methoxymethyl-2-oxo-imidazolidin-1-ylmethyl]-benzoic acid methyl ester (32 mg, 60%).

Sources & evidence

ORD record
ord-d9b8f55b3d3f4566acd2745b444a8f99
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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