HCID 178486879, compound → HCID 178486845, compound

HRID 2384543Notes

Reaction equation

HRID 2384543 reaction equation
[ClH:1].O=[C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:28][CH3:29])=[C:10]([O:13][C@H:14]3[CH2:19][CH2:18][C@H:17]([N:20]4[CH2:25][CH2:24][N:23]([CH3:26])[C:22](=[O:27])[CH2:21]4)[CH2:16][CH2:15]3)[CH:11]=2)[N:6]=[CH:5][NH:4]1>C(#N)C>[ClH:1].[Cl:1][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:28][CH3:29])=[C:10]([O:13][C@H:14]3[CH2:19][CH2:18][C@H:17]([N:20]4[CH2:25][CH2:24][N:23]([CH3:26])[C:22](=[O:27])[CH2:21]4)[CH2:16][CH2:15]3)[CH:11]=2)[N:6]=[CH:5][N:4]=1

Participants

3

Reactant 1

HCID 178486879HCID 178486879, compound

Product 1

HCID 178486845HCID 178486845, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

210 g of 3,4-dihydro-4-oxo-6-[trans-4-(4-methyl-3-oxo-piperazin-1-yl)-cyclohexyloxy]-7-methoxy-quinazoline hydrochloride [(V) HCl] in 1680 ml acetonitrile are refluxed and 840 ml of solvent are distilled off (elimination of traces of water). 221.4 g triphenylphosphine in 840 ml dioxane are added. 119.4 g of N-chlorosuccinimide in 600 ml acetonitrile are added. 260 ml acetonitrile are added. The mixture is stirred for 45 min at 80° C. and then cooled to 30° C. 8.94 ml of water and 420 ml dioxane are added. The precipitate is filtered off under protective gas and washed with 1200 ml THF. The product is precipitated as the hydrochloride and is processed further without drying. A small amount was dried and the yield can be calculated as approx. 210 g in relation thereto.

Workup

  1. distillation840 ml of solvent are distilled off (elimination of traces of water)
  2. addition221.4 g triphenylphosphine in 840 ml dioxane are added
  3. addition119.4 g of N-chlorosuccinimide in 600 ml acetonitrile are added
  4. addition260 ml acetonitrile are added
  5. temperaturecooled to 30° C
  6. addition8.94 ml of water and 420 ml dioxane are added
  7. filtrationThe precipitate is filtered off under protective gas
  8. washwashed with 1200 ml THF
  9. customThe product is precipitated as the hydrochloride
  10. customwithout drying
  11. customA small amount was dried
  12. customthe yield can

Sources & evidence

ORD record
ord-37c5ab457e844997bfe8dfddb350541d
Source dataset
uspto-grants-2012_09
Patent number
US08263768B2

Reaction notes

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