Methyl 1-(2-oxoethyl)cyclohexanecarboxylate → 1-{2-[2-methyl-6-((2S,3'R)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-ylamino]-ethyl}-cyclohexanecarboxylic acid methyl ester

HRID 2401128Notes

Reaction equation

HRID 2401128 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:11][CH:12]=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[CH3:14][C:15]1[C:20]([NH2:21])=[CH:19][CH:18]=[C:17]([N:22]2[CH2:26][CH2:25][C@@H:24]([N:27]3[CH2:31][CH2:30][CH2:29][C@@H:28]3[CH3:32])[CH2:23]2)[N:16]=1>>[CH3:1][O:2][C:3]([C:5]1([CH2:11][CH2:12][NH:21][C:20]2[C:15]([CH3:14])=[N:16][C:17]([N:22]3[CH2:26][CH2:25][C@@H:24]([N:27]4[CH2:31][CH2:30][CH2:29][C@@H:28]4[CH3:32])[CH2:23]3)=[CH:18][CH:19]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

3

Reactant 2

HCID 23021124Methyl 1-(2-oxoethyl)cyclohexanecarboxylateHCID 674804612-methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]pyridin-3-amine

Product 1

HCID 712808731-{2-[2-methyl-6-((2S,3'R)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-ylamino]-ethyl}-cyclohexanecarboxylic acid methyl ester

Procedure

The title compound was synthesized in essentially the same manner using the procedures as set forth in Step 1 of Example 1, by condensing 1-(2-oxo-ethyl)-cyclohexanecarboxylic acid methyl ester (41 mg, 0.22 mmol) and 2-methyl-6-((2S,3′R)-2-methyl-[1,3′]bipyrrolidinyl-1′-yl)-pyridin-3-ylamine to obtain 94 mg of a crude solid, which was used in the next step of the reaction without further purification.

Sources & evidence

ORD record
ord-cb2f1da5c3e54bfc836846fbf5dcf83c
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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