Imidazole → HCID 58911254, compound

HRID 2358237Notes

Reaction equation

HRID 2358237 reaction equation
S(Cl)(Cl)=O.[Br:5][CH2:6][CH2:7][CH2:8][C:9]([NH:11][C:12]1(O)[CH2:14][CH2:13]1)=[O:10].[NH:16]1[CH:20]=[CH:19][N:18]=[CH:17]1.CCN(CC)CC>C(Cl)(Cl)Cl.C1COCC1>[Br:5][CH2:6][CH2:7][CH2:8][C:9]([NH:11][C:12]1([N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[CH2:14][CH2:13]1)=[O:10]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 58911275HCID 58911275, compound

Product 1

HCID 58911254HCID 58911254, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 50 ml three necked flask fitted with a magnetic stirrer, under inert atmosphere, thionyl chloride (2.72 g, 0.023 mmol) is added to the crude 4-bromo-N-(1-hydroxy-cyclopropyl)-butyramide a16 (2.3 g, 9.13 mmol) in CHCl3 (20 ml). After 3 h at room temperature, the light orange reaction mixture is evaporated, diluted in THF (5 ml) and added into another 50 ml three necked flask fitted with a magnetic stirrer, under inert atmosphere, containing a solution of imidazole (0.622 g, 9.1 mmol) and Et3N (2.8 g) in THF (20 ml) at room temperature. After 6 h, the reaction mixture is cooled down to 0° C., filtrated and concentrated in vacuo to give the crude 4-bromo-N-(1-imidazol-1-yl-cyclopropyl)-butyramide a18 (2.76 g) which is used in the next step without any further purification.

Workup

  1. customthe light orange reaction mixture is evaporated
  2. additiondiluted in THF (5 ml)
  3. additionadded into another 50 ml three necked flask
  4. customfitted with a magnetic stirrer, under inert atmosphere
  5. waitAfter 6 h
  6. filtrationfiltrated
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32ccf7559a01469d845e939c618bdbf0
Source dataset
uspto-grants-2010_07
Patent number
US07763644B2

Reaction notes

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