Diisopropylethylamine → HCID 67437879, compound

HRID 340146Notes

Reaction equation

HRID 340146 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([C:8]([O:10][C@H:11]2[C:15]3[N:16]=[CH:17][N:18]=[C:19](Cl)[C:14]=3[C@H:13]([CH3:21])[CH2:12]2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:24]1([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29][CH2:28]N[CH2:26][CH2:25]1.[CH:38](N(CC)C(C)C)(C)C>CC(O)C>[CH3:21][C@H:13]1[C:14]2[C:19]([CH:38]3[CH2:28][CH2:29][CH2:30][N:24]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:25][CH2:26]3)=[N:18][CH:17]=[N:16][C:15]=2[C@H:11]([O:10][C:8](=[O:9])[C:7]2[CH:22]=[CH:23][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 86651804(5R,7R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate

Product 1

HCID 67437879HCID 67437879, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

(5R,7R)-4-Chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate (65 mg, 0.195 mmol) was dissolved in i-PrOH (5 mL), and then tert-butyl 1,4-diazepane-1-carboxylate (51 mg, 0.253 mmol) was added. N,N-Diisopropylethylamine (49 mg, 0.350 mmol) was added, and the reaction mixture was heated to 80° C. for 12 hours, after which the solvents were removed under reduced pressure. The resulting residue was taken up into EtOAc and then washed twice with water and once with brine. The organic portion was dried over magnesium sulfate, filtered, and then concentrated. The resulting residue was purified via silica gel chromatography to give tert-butyl 4-((5R,7R)-5-methyl-7-(4-nitrobenzoyloxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)azepane-1-carboxylate (78 mg, 81%). LCMS (APCI+) M+=498.1, Rt=3.81 min.

Workup

  1. customafter which the solvents were removed under reduced pressure
  2. washwashed twice with water and once with brine
  3. dry with materialThe organic portion was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified via silica gel chromatography

Sources & evidence

ORD record
ord-72f42fa081864eaca5e3b61f54093a3a
Source dataset
uspto-grants-2014_11
Patent number
US08895566B2

Reaction notes

Loading…