Acetonitrile → HCID 178492288, compound

HRID 538039Notes

Reaction equation

HRID 538039 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[NH:7]C(=O)O[C:10](=[O:11])[C:5]=2[CH:4]=1.CC#N.[NH2:18][CH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([C:26]([N:28]2[CH2:33][CH2:32][N:31]([C:34](=[O:38])[CH:35]([CH3:37])[CH3:36])[CH2:30][CH2:29]2)=[O:27])[CH2:22][CH2:21]1>>[NH2:7][C:6]1[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[C:10]([NH:18][CH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([C:26]([N:28]2[CH2:33][CH2:32][N:31]([C:34](=[O:38])[CH:35]([CH3:36])[CH3:37])[CH2:30][CH2:29]2)=[O:27])[CH2:22][CH2:21]1)=[O:11]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 2944796-methoxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneHCID 178454419HCID 178454419, compound

Product 1

HCID 178492288HCID 178492288, compoundYield 70.2%

Conditions

Temperature
50 °C

Procedure

To a solution of 6-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione (96 mg, 0.5 mmol) in CH3CN (5 mL) K2CO3 (140 mg, 1 mmol) and 1-[trans-4-(4-Aminomethyl-cyclohexanecarbonyl)-piperazin-1-yl]-2-methyl-propan-1-one (148 mg, 0.5 mmol) were added and the reaction was heated at 50° C. for 16 h. The solvent was removed under reduced pressure, 5 mL of 0.4M Na2CO3 solution were added and the mixture was stirred for 1 h. Then 5 mL of DCM were added, the organic phase collected, dried over Na2SO4 and the solvent removed under reduced pressure. 156 mg of the titled product were obtained (yield=68%).

Workup

  1. customThe solvent was removed under reduced pressure, 5 mL of 0.4M Na2CO3 solution
  2. additionwere added
  3. additionThen 5 mL of DCM were added
  4. customthe organic phase collected
  5. dry with materialdried over Na2SO4
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-69e8e930a5ff432495dd142b69ae46c2
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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