HCID 178499628, compound → HCID 178515403, compound

HRID 2070907Notes

Reaction equation

HRID 2070907 reaction equation
[NH2:1][C:2]1[C:3]([CH2:26][C:27]([O:29]C)=O)=[N:4][CH:5]=[C:6]([NH:8][C:9]2[N:25]=[C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([NH:17][C@H:18]4[CH2:23][CH2:22][C@@H:21]([OH:24])[CH2:20][CH2:19]4)[N:11]3[N:10]=2)[CH:7]=1>ClCCl.CO.[Ni]>[OH:24][C@@H:21]1[CH2:22][CH2:23][C@H:18]([NH:17][C:16]2[N:11]3[N:10]=[C:9]([NH:8][C:6]4[CH:7]=[C:2]5[NH:1][C:27](=[O:29])[CH2:26][C:3]5=[N:4][CH:5]=4)[N:25]=[C:12]3[CH:13]=[CH:14][CH:15]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 1

HCID 178499628HCID 178499628, compound

Product 1

HCID 178515403HCID 178515403, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl cis-2-(3-amino-5-(5-(4-hydroxycyclohexylamino)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)pyridin-2-yl)acetate. To a mixture of diethyl cis-2-(3-amino-5-(5-(4-hydroxycyclohexylamino)-[1,2,4]triazolo[1,5-c]pyridin-2-ylamino)pyridin-2-yl)malonate (120.0 mg, 0.23 mmol) in a mixture of dichloromethane (10 mL) and methanol (50 mL) was added Raney nickel (100 mg), and the mixture was stirred under hydrogen at room temperature for 24 hours. LCMS analysis showed that the major product was the desired product (if the reaction was not completed, just kept the hydrogenation until the reaction was completed). The mixture was filtered, concentrated under reduced pressure, and purified on silica gel column (eluting with 1-2% dichloromethane in methanol) to give methyl cis-2-(3-amino-5-(5-(4-hydroxycyclohexylamino)-[1,2,4]triazolo[1,5-c]pyridin-2-ylamino)pyridin-2-yl)acetate.

Sources & evidence

ORD record
ord-7685d8a235b142e9988205c3f7f6e9d2
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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