4-(2-Methyl-1,3-dioxolan-2-yl)aniline → 4,6-dimethyl-pyrimidine-5-carboxylic acid ((R)-3-{4-[4-(2-methyl-[1,3]dioxolan-2-yl)-phenylamino]-piperidin-1-yl}-butyl)-amide

HRID 1726233Notes

Reaction equation

HRID 1726233 reaction equation
[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1.O=[C:15]1[CH2:20][CH2:19][N:18]([C@H:21]([CH3:25])[CH2:22][C:23]#[N:24])[CH2:17][CH2:16]1.[CH3:26][C:27]1[C:32]([C:33](O)=[O:34])=[C:31]([CH3:36])[N:30]=[CH:29][N:28]=1>>[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH:15]3[CH2:20][CH2:19][N:18]([C@H:21]([CH3:25])[CH2:22][CH2:23][NH:24][C:33]([C:32]4[C:27]([CH3:26])=[N:28][CH:29]=[N:30][C:31]=4[CH3:36])=[O:34])[CH2:17][CH2:16]3)=[CH:9][CH:8]=2)[O:3][CH2:4][CH2:5][O:6]1

Participants

4

Reactant 3

HCID 110739824-(2-Methyl-1,3-dioxolan-2-yl)anilineHCID 149222224,6-Dimethylpyrimidine-5-carboxylic acidHCID 68972438(betaR)-beta-Methyl-4-oxo-1-piperidinepropanenitrile

Product 1

HCID 866021334,6-dimethyl-pyrimidine-5-carboxylic acid ((R)-3-{4-[4-(2-methyl-[1,3]dioxolan-2-yl)-phenylamino]-piperidin-1-yl}-butyl)-amide

Procedure

Using general procedure A with 4-(2-methyl-[1,3]dioxolan-2-yl)-phenylamine (see EXAMPLE 173) (500 mg, 2.79 mmol) and (R)-3-(4-oxo-piperidin-1-yl)-butyronitrile (487 mg, 2.93 mmol), then general procedure J and then using general procedure E with the resulting amine and 4,6-dimethyl-pyrimidine-5-carboxylic acid (123 mg, 0.81 mmol) afforded 4,6-dimethyl-pyrimidine-5-carboxylic acid ((R)-3-{4-[4-(2-methyl-[1,3]dioxolan-2-yl)-phenylamino]-piperidin-1-yl}-butyl)-amide as a pale beige solid (315 mg, 29% over 3 steps).

Sources & evidence

ORD record
ord-c1c35dbc29fe44fa8370992a1f53a21f
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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