Cyclopropylamine → HCID 57551775, compound

HRID 907328Notes

Reaction equation

HRID 907328 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[CH2:5]([N:12]1[CH:21]=[C:20]([CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:28]3[CH:29]=[C:30]([CH:35]=[CH:36][C:37]=3[CH3:38])[C:31](OC)=[O:32])[CH:18]=2)[C:13]1=[O:39])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C([Mg]Cl)(C)C>C1COCC1>[CH2:5]([N:12]1[CH:21]=[C:20]([CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:28]3[CH:29]=[C:30]([CH:35]=[CH:36][C:37]=3[CH3:38])[C:31]([NH:4][CH:1]3[CH2:3][CH2:2]3)=[O:32])[CH:18]=2)[C:13]1=[O:39])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 57551724HCID 57551724, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 57551775HCID 57551775, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of cyclopropylamine (0.18 mL) and the product from step ii) (120 mg) in THF (5 mL) was treated with isopropylmagnesium chloride (2N/THF, 1 mL) and stirred at room temperature for 1 hour. The reaction mixture was quenched with saturated aqueous ammonium chloride (10 mL), and extracted into ethyl acetate (2×10 mL). The organic layer was dried over magnesium sulfate, filtered and evaporated in vacuo. Purification by HPLC gave the title compound as a solid (31 mg).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride (10 mL)
  2. extractionextracted into ethyl acetate (2×10 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by HPLC

Sources & evidence

ORD record
ord-41fa2cb7f4fb487d8e7ae6d95acca8cb
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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