Dimethylamine → (R)-1-(2-(2-Cyclopropylpyrimidin-4-yl)-3H-imidazo[4,5-b]pyridin-5-yl)-N,N-dimethylpiperidine-3-carboxamide

HRID 931200Notes

Reaction equation

[CH3:1][NH:2][CH3:3].C(N(CC)CC)C.[CH:11]1([C:14]2[N:19]=[C:18]([C:20]3[NH:37][C:23]4=[N:24][C:25]([N:28]5[CH2:33][CH2:32][CH2:31][C@@H:30]([C:34](O)=[O:35])[CH2:29]5)=[CH:26][CH:27]=[C:22]4[N:21]=3)[CH:17]=[CH:16][N:15]=2)[CH2:13][CH2:12]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[CH:11]1([C:14]2[N:19]=[C:18]([C:20]3[NH:37][C:23]4=[N:24][C:25]([N:28]5[CH2:33][CH2:32][CH2:31][C@@H:30]([C:34]([N:2]([CH3:3])[CH3:1])=[O:35])[CH2:29]5)=[CH:26][CH:27]=[C:22]4[N:21]=3)[CH:17]=[CH:16][N:15]=2)[CH2:13][CH2:12]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of dimethylamine (175 μmol) in N,N-dimethylformamide (200 μL) was added triethylamine (35 μL, 250 μmol) and (R)-1-(2-(2-cyclopropylpyrimidin-4-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylic acid (200 μL, 50 μmol, 0.25M in N,N-dimethylformamide) followed by 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate (250 μL, 100 μmol, 0.4M in N,N-dimethylformamide). The reaction mixture was stirred at 50° C. for 16 h. The solvent was removed by Speedvac and the residue was purified via HPLC to afford the title compound. MS API-ES+ (M+H) 392; HPLC retention time 2.43 min (Method C).

Workup

customThe solvent was removed by Speedvac
customthe residue was purified via HPLC

Sources & evidence

ORD record: ord-2e9914e33760482eae70801b85798f19
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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