4-Methylpyridine-3-carbaldehyde → [1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-(4-methyl-pyridin-3-ylmethyl)-amine

HRID 1726311Notes

Reaction equation

HRID 1726311 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C@H:10]([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)[CH3:11])(C)(C)C.[CH3:34][C:35]1[CH:40]=[CH:39][N:38]=[CH:37][C:36]=1[CH:41]=O>C(Cl)CCl>[NH2:7][CH2:8][CH2:9][C@H:10]([N:12]1[CH2:13][CH2:14][CH:15]([N:18]([C:19]2[CH:20]=[CH:21][C:22]([O:25][Si:26]([C:29]([CH3:30])([CH3:32])[CH3:31])([CH3:27])[CH3:28])=[CH:23][CH:24]=2)[CH2:41][C:36]2[CH:37]=[N:38][CH:39]=[CH:40][C:35]=2[CH3:34])[CH2:16][CH2:17]1)[CH3:11]

Participants

4

Reactant 2

HCID 124604704-Methylpyridine-3-carbaldehydeHCID 68968850((R)-3-{4-[4-(tert-butyl-dimethyl-silanyloxy)-phenylamino]-piperidin-1-yl}-butyl)-carbamic acid tert-butyl ester

Product 1

HCID 68970307[1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-(4-methyl-pyridin-3-ylmethyl)-amineYield 17%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Using general procedure A with ((R)-3-{4-[4-(tert-butyl-dimethyl-silanyloxy)-phenylamino]-piperidin-1-yl}-butyl)-carbamic acid tert-butyl ester (see EXAMPLE 233) (796 mg, 2.10 mmol) and 4-methyl-3-pyridinecarboxaldehyde (see EXAMPLE 356) (367 mg, 3.00 mmol) in ClCH2CH2Cl (6 mL) followed by general procedure C afforded [1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-(4-methyl-pyridin-3-ylmethyl)-amine (130 mg, 17% over 2 steps) as a white foam.

Sources & evidence

ORD record
ord-7e192d42ea43462e8ef294a0ec52e501
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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