Sodium Bicarbonate → HCID 57954431, compound

HRID 221374Notes

Reaction equation

HRID 221374 reaction equation
C(O[C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[N:7]=1)=[O:5])C.[CH2:17]([CH:22]1[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]1)[CH2:18][CH2:19][CH2:20][CH3:21].C([Al](CC)CC)C.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl>[CH2:17]([CH:22]1[CH2:23][CH2:24][CH:25]([NH:28][C:4]([C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=3)[N:7]=2)=[O:5])[CH2:26][CH2:27]1)[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 13783029Cyclohexanamine, 4-pentyl-HCID 16682930TriethylaluminumHCID 16767420HCID 16767420, compound

Product 1

HCID 57954431HCID 57954431, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-pyridin-4-yl-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester (50.5 mg, 0.23 mmol) and 4-pentylcyclohexylamine (39 mg, 0.23 mmol) in anhydrous toluene (2 ml) was treated with triethylaluminium (345 μl of a 2M solution in hexanes, 0.69 mmol). After stirring at rt for 18 h, saturated aqueous NaHCO3 (2 ml) was added and the mixture diluted with CH2Cl2 (25 ml). The organic phase was separated, washed with brine (5 ml) and dried (MgSO4). The solvent was evaporated and the residue purified by flash chromatography to afford the title compound: RT=4.14 min; m/z (ES+)=343.2 [M+]+.

Workup

  1. customThe organic phase was separated
  2. washwashed with brine (5 ml)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated
  5. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-ba0fd363aa7f4327a8d40be6875a7a71
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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