Sodium Methoxide → HCID 178494002, compound

HRID 503804Notes

Reaction equation

C([C:3]1[N:41]=[C:6]2[N:7]=[C:8]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][N:24]4[CH2:29][CH2:28][CH:27]([C:30]5[N:34]=[C:33]([C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=6)[NH:32][N:31]=5)[CH2:26][CH2:25]4)=[CH:19][CH:18]=3)[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:10][N:5]2[N:4]=1)#C.[CH3:42][O-:43].[Na+]>CO.O.ClCCl>[CH3:42][O:43][C:3]1[N:41]=[C:6]2[N:7]=[C:8]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][N:24]4[CH2:29][CH2:28][CH:27]([C:30]5[N:34]=[C:33]([C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=6)[NH:32][N:31]=5)[CH2:26][CH2:25]4)=[CH:19][CH:18]=3)[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:10][N:5]2[N:4]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To 110 mg 2-bromo-6-phenyl-5-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[1,5-a]pyrimidine (prepared as described under example 53) in 5 ml methanol are added 1.11 ml of a sodium methoxide solution (25% in methanol). The reaction mixture is heated to 55° C. for 3.5 hours and diluted with water and dichloromethane. The phases are separated and the water layer is extracted with dichloromethane. The combined organic layers are dried over Na2SO4 and the solvent are removed by evaporation. The residue is purified by RP HPLC (water, 10 mM NH4COOH, pH 3.7/ACN) to yield the desired compound.

Workup

customThe phases are separated
extractionthe water layer is extracted with dichloromethane
dry with materialThe combined organic layers are dried over Na2SO4
customthe solvent are removed by evaporation
customThe residue is purified by RP HPLC (water, 10 mM NH4COOH, pH 3.7/ACN)

Sources & evidence

ORD record: ord-fdb30256e66a427bb912ac154a159706
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776864B2

Reaction notes

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