1,1'-Carbonyldiimidazole → HCID 44477247, compound

HRID 2361665Notes

Reaction equation

HRID 2361665 reaction equation
O[C:2]1([OH:9])[CH2:5][CH:4]([C:6]([OH:8])=O)[CH2:3]1.C(Cl)Cl.CN(C=O)C.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH:30]1([N:34]2[CH2:40][CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH2:33][CH2:32][CH2:31]1>C(Cl)Cl>[CH:30]1([N:34]2[CH2:40][CH2:39][CH2:38][N:37]([C:6]([CH:4]3[CH2:3][C:2](=[O:9])[CH2:5]3)=[O:8])[CH2:36][CH2:35]2)[CH2:33][CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 22350042dichloromethane N,N-dimethylformamideHCID 55302371HCID 55302371, compoundHCID 574239531-Cyclobutyl-[1,4]diazepane

Product 1

HCID 44477247HCID 44477247, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3,3-dihydroxycyclobutanecarboxylic acid (80 mg, 0.61 mmol) in 4:1 DCM/DMF (2.5 ml) was added CDI (103 mg, 0.64 mmol) at RT. The mixture was stirred for 1.5 h at RT and 1-cyclobutyl-1,4-diazepane (98 mg, 0.64 mmol) was added. The resulting solution was stirred at RT for 3 H, diluted with DCM (20 ml) and washed with 1:1 H2O/brine (20 ml). The organic layer was dried (Na2SO4), filtered and concentrated at reduced pressure. Purification by silica gel FCC (eluting with DCM/MeOH/NH3 90:10:1) provided the title compound as colourless oil (84 mg, 56%).

Workup

  1. stirringThe resulting solution was stirred at RT for 3 H
  2. washwashed with 1:1 H2O/brine (20 ml)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure
  6. customPurification
  7. washby silica gel FCC (eluting with DCM/MeOH/NH3 90:10:1)

Sources & evidence

ORD record
ord-a93b5178fabc4dc98073938d246ecc4a
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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