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 1909036Notes

Reaction equation

HRID 1909036 reaction equation
[Li+].CC([N-]C(C)C)C.CO[C:11](=[O:31])[C:12]1[CH:22]=[CH:21][C:15]([C:16]([N:18](C)C)=O)=[C:14]([C:23]2[C:24]([CH3:30])=[N:25][N:26]([CH3:29])[C:27]=2[CH3:28])[CH:13]=1.CN(C[N:36]1[C:40]2=[N:41][C:42]([N:45]3[CH2:50][CH2:49][CH:48]([N:51]([CH3:53])[CH3:52])[CH2:47][CH2:46]3)=[CH:43][CH:44]=[C:39]2[N:38]=[CH:37]1)C>>[CH3:52][N:51]([CH3:53])[CH:48]1[CH2:49][CH2:50][N:45]([C:42]2[N:41]=[C:40]3[NH:36][C:37]([C:11]([C:12]4[CH:22]=[CH:21][C:15]([C:16]#[N:18])=[C:14]([C:23]5[C:24]([CH3:30])=[N:25][N:26]([CH3:29])[C:27]=5[CH3:28])[CH:13]=4)=[O:31])=[N:38][C:39]3=[CH:44][CH:43]=2)[CH2:46][CH2:47]1

Participants

4

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 66599461N,N-Dimethyl-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-terephthalamic 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 N,N-Dimethyl-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 529.3036 (M+H)+.

Sources & evidence

ORD record
ord-810047ca8a2e4c089fe55755060ab15d
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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