Acetic Acid → HCID 178525786, compound

HRID 931199Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([OH:17])=[O:16])[CH2:10]2)=[N:6][C:7]=1[NH2:8].CN(C)C=O.[CH:23]1([C:26]2[N:31]=[C:30]([CH:32]=O)[CH:29]=[CH:28][N:27]=2)[CH2:25][CH2:24]1.C(O)(=O)C>>[CH:23]1([C:26]2[N:31]=[C:30]([C:32]3[NH:8][C:7]4=[N:6][C:5]([N:9]5[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([OH:17])=[O:16])[CH2:10]5)=[CH:4][CH:3]=[C:2]4[N:1]=3)[CH:29]=[CH:28][N:27]=2)[CH2:25][CH2:24]1

Participants

Reactant 4

HCID 176Acetic Acid

HCID 6228Dimethylformamide2×

HCID 299398122-Cyclopropylpyrimidine-4-carbaldehyde

HCID 117966601(R)-1-(5,6-diaminopyridin-2-yl)piperidine-3-carboxylic acid

Product 1

HCID 178525786HCID 178525786, compound

Conditions

Temperature: 60 °C

Procedure

To a solution of (R)-1-(5,6-diaminopyridin-2-yl)piperidine-3-carboxylic acid in N,N-dimethylformamide (49 mL, 12.25 mmol, 0.25M) was added a solution of 2-cyclopropylpyrimidine-4-carbaldehyde in N,N-dimethylformamide (49 mL, 12.25 mmol, 0.25M) followed by acetic acid (7.35 mL, 122.5 mmol). The reaction mixture was stirred at 60° C. for 16 h. The solvent was removed under reduced pressure and the residue was purified via HPLC to afford (R)-1-(2-(2-cyclopropylpyrimidin-4-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylic acid.

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified via HPLC

Sources & evidence

ORD record: ord-6d9ea41b497d464fa9dafa4aea2b46d7
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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