Sodium Cyanate → 1-(2,3-dimethoxy-quinoxalin-6-ylmethyl)-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

HRID 641815Notes

Reaction equation

HRID 641815 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:15][NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]#[CH:26])=[CH:19][C:18]=3[C:27]([C:29]3[CH:34]=[CH:33][C:32]([CH:35]([CH3:37])[CH3:36])=[CH:31][CH:30]=3)=O)[CH:9]=2)[N:4]=1.[O-:38][C:39]#[N:40].[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:15][N:16]3[C:17]4[C:18](=[CH:19][C:20]([O:23][CH2:24][C:25]#[CH:26])=[CH:21][CH:22]=4)[C:27]([C:29]4[CH:34]=[CH:33][C:32]([CH:35]([CH3:36])[CH3:37])=[CH:31][CH:30]=4)=[N:40][C:39]3=[O:38])[CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 517096Sodium CyanateHCID 11755527{2-[(2,3-Dimethoxy-quinoxalin-6-ylmethyl)-amino]-5-prop-2-ynyloxy-phenyl}-(4-isopropyl-phenyl)-methanone

Product 1

HCID 592591551-(2,3-dimethoxy-quinoxalin-6-ylmethyl)-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 52 mg (0.105 mmol) {2-[(2,3-dimethoxy-quinoxalin-6-ylmethyl)-amino]-5-prop-2-ynyloxy-phenyl}-(4-isopropyl-phenyl)-methanone in 1 ml acetic acid is added 14 mg (0.210 mmol) sodium cyanate. After stirring for 2 h the solvent is removed in vacuo and the residue is partitioned between CH2Cl2 and water. The organic layer is extracted with 2 M sodium hydroxide and evaporated. Purification of the crude product by flash-chromatography (ethyl acetate/hexanes 9:1) affords a yellow oil.

Workup

  1. customis removed in vacuo
  2. customthe residue is partitioned between CH2Cl2 and water
  3. extractionThe organic layer is extracted with 2 M sodium hydroxide
  4. customevaporated
  5. customPurification of the crude product by flash-chromatography (ethyl acetate/hexanes 9:1)
  6. customaffords a yellow oil

Sources & evidence

ORD record
ord-9889de2058ab4fb886ac7395d298035e
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

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