Water → HCID 70975558, compound

HRID 1190819Notes

Reaction equation

HRID 1190819 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]3[N:21]([CH2:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=4[O:34][CH3:35])[C:22](=[O:24])[NH:23][C:15]=23)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:43]([C:45]1[CH:52]=[CH:51][CH:50]=[CH:49][C:46]=1[CH2:47]Br)#[N:44].O>CN(C=O)C>[C:1]([O:5][C:6](=[O:36])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]3[N:21]([CH2:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=4[O:34][CH3:35])[C:22](=[O:24])[N:23]([CH2:47][C:46]4[CH:49]=[CH:50][CH:51]=[CH:52][C:45]=4[C:43]#[N:44])[C:15]=23)[CH2:9]1)([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 895992-(Bromomethyl)benzonitrileHCID 70975548HCID 70975548, compound

Product 1

HCID 70975558HCID 70975558, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.03 g (R)-1-[3-(2,4-dimethoxybenzyl)-5-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl]piperidine-3-carbamic acid tert-butyl ester (2.07 mmol) was dissolved in 5 mL DMF. 0.57 g potassium carbonate (4.14 mmol) was added, and then 0.45 g 2-cyano-benzyl bromide (2.28 mmol) was added. The reaction solution was stirred for 5 h at room temperature, and slowly poured into 100 mL water to precipitate a solid, filtrated, and dried to afford 1.24 g crude product with a yield of 97.9%.

Workup

  1. customto precipitate a solid
  2. filtrationfiltrated
  3. customdried

Sources & evidence

ORD record
ord-5436d273418a4ef89000c1f1846e44d8
Source dataset
uspto-grants-2014_03
Patent number
US08680089B2

Reaction notes

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