Lithium diisopropylamide → Benzonitrile, 4-[[5-[4-(diMethylaMino)-1-piperidinyl]-3H-iMidazo[4,5-b]pyridin-2-yl]carbonyl]-2-(1,3,5-triMethyl-1H-pyrazol-4-yl)-

HRID 1909035Notes

Reaction equation

HRID 1909035 reaction equation
[Li+].CC([N-]C(C)C)C.CO[C:11](=[O:29])[C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=O)=[C:14]([C:21]2[C:22]([CH3:28])=[N:23][N:24]([CH3:27])[C:25]=2[CH3:26])[CH:13]=1.CN(C[N:34]1[C:38]2=[N:39][C:40]([N:43]3[CH2:48][CH2:47][CH:46]([N:49]([CH3:51])[CH3:50])[CH2:45][CH2:44]3)=[CH:41][CH:42]=[C:37]2[N:36]=[CH:35]1)C>>[CH3:50][N:49]([CH3:51])[CH:46]1[CH2:47][CH2:48][N:43]([C:40]2[N:39]=[C:38]3[NH:34][C:35]([C:11]([C:12]4[CH:20]=[CH:19][C:15]([C:16]#[N:18])=[C:14]([C:21]5[C:22]([CH3:28])=[N:23][N:24]([CH3:27])[C:25]=5[CH3:26])[CH:13]=4)=[O:29])=[N:36][C:37]3=[CH:42][CH:41]=2)[CH2:44][CH2:45]1

Participants

4

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 66599667[1-(3-dimethylaminomethyl-3H-imidazo[4,5-b]pyridin-5-yl)-piperidin-4-yl]-dimethyl-amineHCID 665997743-(1,3,5-Trimethyl-1H-pyrazol-4-yl)-terephthalamic acid methyl ester

Product 1

HCID 178434016Benzonitrile, 4-[[5-[4-(diMethylaMino)-1-piperidinyl]-3H-iMidazo[4,5-b]pyridin-2-yl]carbonyl]-2-(1,3,5-triMethyl-1H-pyrazol-4-yl)-

Procedure

Following General procedure P (LDA metallation, ketone formation and in situ deprotection) using 3-(1,3,5-Trimethyl-1H-pyrazol-4-yl)-terephthalamic acid methyl ester and [1-(3-dimethylaminomethyl-3H-imidazo[4,5-b]pyridin-5-yl)-piperidin-4-yl]-dimethyl-amine to give 4-[5-(4-dimethylamino-piperidin-1-yl)-3H-imidazo[4,5-b]pyridine-2-carbonyl]-2-(1,3,5-trimethyl-1H-pyrazol-4-yl)-benzonitrile. (84%). HRMS m/z 501.2721 (M+H)+.

Sources & evidence

ORD record
ord-e10d8f992ded4ec29fb0c16de5deddc8
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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