Sodium Hydroxide → HCID 66628539, compound

HRID 1622217Notes

Reaction equation

HRID 1622217 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[O:15][C:14](S)=[N:13][N:12]=3)[CH:9]=2)[CH:4]=[CH:3]1.[N:17]12[CH2:25][CH2:24][CH:21]([CH2:22][CH2:23]1)[NH:20][CH2:19][CH2:18]2.[OH-].[Na+].[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>CO.C(OCC)C.C(O)CC>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32].[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[O:15][C:14]([N:20]4[CH:21]5[CH2:24][CH2:25][N:17]([CH2:23][CH2:22]5)[CH2:18][CH2:19]4)=[N:13][N:12]=3)[CH:9]=2)[CH:4]=[CH:3]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 3984071,4-Diazabicyclo(3.2.2)nonaneHCID 444972Fumaric AcidHCID 178480039HCID 178480039, compound

Product 1

HCID 66628539HCID 66628539, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 10311-PropanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-(1-methyl-1H-indol-6-yl)[1,3,4]oxadiazole-2-thiol (1.25 g, 5.41 mmol), 1,4-Diazabicyclo[3.2.2]nonane (0.69 g, 5.41 mmol) and 1-propanol (5 ml) was stirred at 130° C. for 15 h. The reaction-mixture was allowed to cool to room-temperature. Aqueous sodium hydroxide (1 M) was added and the mixture was extracted twice with chloroform. The mixture was extracted twice with aqueous hydrochloric acid. The aqueous phase was washed with chloroform and was made alkaline by adding sodium hydroxide (4 M), followed by extraction three times with chloroform. The free base was isolated as a brown oil. Yield 500 mg (29%) The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Yield 250 mg (36%). LC-ESI-HRMS of [M+H]+ shows 324.1823 Da. Calc. 324.182435 Da, dev. −0.4 ppm.

Workup

  1. temperatureto cool to room-temperature
  2. extractionthe mixture was extracted twice with chloroform
  3. extractionThe mixture was extracted twice with aqueous hydrochloric acid
  4. washThe aqueous phase was washed with chloroform
  5. additionby adding sodium hydroxide (4 M)
  6. extractionfollowed by extraction three times with chloroform
  7. customThe free base was isolated as a brown oil

Sources & evidence

ORD record
ord-b4d2286c675d4486a57fa6f56480777a
Source dataset
uspto-grants-2014_07
Patent number
US08778928B2

Reaction notes

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