3-Methoxypyrrolidine → 6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid [3-(3-methoxy-pyrrolidine-1-carbonyl)-1-methyl-1H-pyrazol-4-yl]-amide

HRID 467670Notes

Reaction equation

HRID 467670 reaction equation
[CH3:1][O:2][CH:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.C[O:9][C:10]([C:12]1[C:16]([NH:17][C:18]([C:20]2[C:25]([NH:26][C:27]3[CH:28]=[N:29][CH:30]=[N:31][CH:32]=3)=[CH:24][CH:23]=[C:22]([CH:33]3[CH2:35][CH2:34]3)[N:21]=2)=[O:19])=[CH:15][N:14]([CH3:36])[N:13]=1)=O>>[CH3:1][O:2][CH:3]1[CH2:7][CH2:6][N:5]([C:10]([C:12]2[C:16]([NH:17][C:18]([C:20]3[C:25]([NH:26][C:27]4[CH:28]=[N:29][CH:30]=[N:31][CH:32]=4)=[CH:24][CH:23]=[C:22]([CH:33]4[CH2:35][CH2:34]4)[N:21]=3)=[O:19])=[CH:15][N:14]([CH3:36])[N:13]=2)=[O:9])[CH2:4]1

Participants

3

Reactant 2

HCID 113554473-MethoxypyrrolidineHCID 700992004-{[6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carbonyl]-amino}-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester

Product 1

HCID 585483406-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid [3-(3-methoxy-pyrrolidine-1-carbonyl)-1-methyl-1H-pyrazol-4-yl]-amideYield 23%

Procedure

According to the general method described in step 5 of example 27, reaction of 3-methoxypyrrolidine with 4-{[6-cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carbonyl]-amino}-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester provided the title compound (23%) as amorphous yellow solid.

Sources & evidence

ORD record
ord-e7eab241f0444b4dbb5197139f3f2283
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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