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 1909048Notes

Reaction equation

HRID 1909048 reaction equation
[Li+].CC([N-]C(C)C)C.CO[C:11](=[O:28])[C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[C:14]([C:20]2[C:21]([CH3:27])=[N:22][N:23]([CH3:26])[C:24]=2[CH3:25])[CH:13]=1.CN(C[N:33]1[C:37]2=[N:38][C:39]([N:42]3[CH2:47][CH2:46][CH:45]([N:48]([CH3:50])[CH3:49])[CH2:44][CH2:43]3)=[CH:40][CH:41]=[C:36]2[N:35]=[CH:34]1)C>>[CH3:49][N:48]([CH3:50])[CH:45]1[CH2:46][CH2:47][N:42]([C:39]2[N:38]=[C:37]3[NH:33][C:34]([C:11]([C:12]4[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[C:14]([C:20]5[C:21]([CH3:27])=[N:22][N:23]([CH3:26])[C:24]=5[CH3:25])[CH:13]=4)=[O:28])=[N:35][C:36]3=[CH:41][CH:40]=2)[CH2:43][CH2:44]1

Participants

4

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 665996514-cyano-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-benzoic acid methyl esterHCID 66599667[1-(3-dimethylaminomethyl-3H-imidazo[4,5-b]pyridin-5-yl)-piperidin-4-yl]-dimethyl-amine

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 4-cyano-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-benzoic 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 483.2620 (M+H)+.

Sources & evidence

ORD record
ord-7990086372a84eb68d66fbd66bceb39f
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

Loading…