Triphenylphosphine → 4-{3-[3-(cyclopentyloxy)-4-methoxybenzyl]-6-(2,2-difluoro-ethoxy)-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl}piperidine-1-carbaldehyde

HRID 403564Notes

Reaction equation

HRID 403564 reaction equation
[CH3:1]C(OC(/N=N/C(OC(C)C)=O)=O)C.[F:15][CH:16]([F:39])[CH2:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]([CH:29]1[CH2:34][CH2:33][N:32]([CH:35]=[O:36])[CH2:31][CH2:30]1)[C:24](=[O:37])[NH:23][C:22]2=[O:38].[CH:40]1([O:45][C:46]2[CH:51]=[CH:50][C:49](CO)=[CH:48][C:47]=2[O:54][CH3:55])[CH2:44][CH2:43][CH2:42][CH2:41]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[CH:40]1([O:45][C:46]2[CH:51]=[C:50]([CH:49]=[CH:48][C:47]=2[O:54][CH3:55])[CH2:1][N:23]2[C:22](=[O:38])[C:21]3[C:26](=[CH:27][CH:28]=[C:19]([O:18][CH2:17][CH:16]([F:15])[F:39])[CH:20]=3)[N:25]([CH:29]3[CH2:34][CH2:33][N:32]([CH:35]=[O:36])[CH2:31][CH2:30]3)[C:24]2=[O:37])[CH2:41][CH2:42][CH2:43][CH2:44]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 252533494-[6-(2,2-Difluoroethoxy)-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl]piperidine-1-carbaldehydeHCID 28562168(4-(Cyclopentyloxy)-3-methoxyphenyl)methanol

Product 1

HCID 252538164-{3-[3-(cyclopentyloxy)-4-methoxybenzyl]-6-(2,2-difluoro-ethoxy)-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl}piperidine-1-carbaldehydeYield 35.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.172 g of DIAD is added to a solution of 0.15 g of 4-[6-(2,2-difluoroethoxy)-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl]piperidine-1-carbaldehyde obtained in stage 3.7, 0.142 g of [4-(cyclopentyloxy)-3-methoxyphenyl]methanol and 0.223 g of PPh3 in 3 ml of anhydrous THF. The mixture is stirred at AT for 12 h 00 and then at 60° C. for 1 h 00. It is evaporated under reduced pressure and the residue is purified on silica gel, elution being carried out with AcOEt, to give 0.083 g of the expected product.

Workup

  1. waitat 60° C. for 1 h 00
  2. customIt is evaporated under reduced pressure
  3. customthe residue is purified on silica gel, elution

Sources & evidence

ORD record
ord-ce895eb9035440ec878a712bfd3ea895
Source dataset
uspto-grants-2014_06
Patent number
US08748441B2

Reaction notes

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