2-Methylpropanimidamide hydrochloride → HCID 178440203, compound

HRID 1917262Notes

Reaction equation

HRID 1917262 reaction equation
Cl.C(O[C:5]([CH:7]1[C:11](=O)[CH2:10][N:9]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8]1)=[O:6])C.Cl.[C:21]([NH2:26])(=[NH:25])[CH:22]([CH3:24])[CH3:23].CC([O-])(C)C.[K+]>C(O)(C)(C)C>[CH2:13]([N:9]1[CH2:8][C:7]2[C:5]([OH:6])=[N:26][C:21]([CH:22]([CH3:24])[CH3:23])=[N:25][C:11]=2[CH2:10]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 27820532-Methylpropanimidamide hydrochlorideHCID 23665647Potassium tert-butoxideHCID 66616389HCID 66616389, compound

Product 1

HCID 178440203HCID 178440203, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-benzyl-4-oxo-pyrrolidine-3-carboxylic acid ethyl ester hydrochloride (U.S. Pat. No. 3,312,716; 0.568 g, 2.30 mmol) in tert-BuOH was added isobutyramidine hydrochloride (0.282 g, 2.30 mmol) and KOtBu (0.516 g, 4.6 mmol). After heating for 6 h at 100° C., the reaction was cooled to rt, concentrated, diluted with water and washed with Et2O. The organic layer discarded. The aqueous layer was adjusted to pH 7 and extracted with Et2O. The organic layers were then dried and concentrated to give 0.145 g (23%) of the title compound of yellow solid that was used without further purification.

Workup

  1. temperaturethe reaction was cooled to rt
  2. concentrationconcentrated
  3. additiondiluted with water
  4. washwashed with Et2O
  5. extractionextracted with Et2O
  6. customThe organic layers were then dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-03d598a0e5bb43b9b35ada996fe165bd
Source dataset
uspto-grants-2013_12
Patent number
US08618288B2

Reaction notes

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