Toluene → HCID 59732028, compound

HRID 2378604Notes

Reaction equation

HRID 2378604 reaction equation
[NH2:1][C@H:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][C:5]2[CH:17]=[C:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([CH3:21])=[CH:20][C:4]=2[CH2:3]1.[C:30](=O)(O)[O-:31].[Na+].C(Cl)(Cl)=O.C1(C)C=CC=CC=1.C(O)(=O)C.[O:50]=[C:51]1[N:60]([CH:61]2[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]2)[CH2:59][C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[NH:52]1>ClCCl>[CH2:10]([N:7]1[C:8](=[O:9])[C@H:2]([NH:1][C:30]([N:64]2[CH2:65][CH2:66][CH:61]([N:60]3[CH2:59][C:58]4[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=4)[NH:52][C:51]3=[O:50])[CH2:62][CH2:63]2)=[O:31])[CH2:3][C:4]2[CH:20]=[C:19]([CH3:21])[C:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[CH:17][C:5]=2[CH2:6]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 59732020HCID 59732020, compoundHCID 67318551HCID 67318551, compound

Product 1

HCID 59732028HCID 59732028, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-tert-Butyl 4-amino-2-benzyl-7-methyl-3-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-ylcarbamate (155 mg, 0.39 mmol) was dissolved in dichloromethane (10 mL). Aqueous sodium bicarbonate (10 mL) was added to the mixture. A solution of 20% phosgene in toluene (230 μL, 0.43 mmol) was added to the mixture with vigorous stirring. Reaction stirred at room temperature for 20 minutes. 4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl) piperidine acetate (140 mg, 0.48 mmol) was added to the mixture. Reaction stirred at room temperature for 1 hour. Reaction layers were partitioned. Organic layer was washed successively with 1N hydrochloric acid and brine. Organic was dried (magnesium sulfate), filtered and concentrated in vacuo. Title compound was obtained as off-white solid in 94% yield. MS m/e (M+H)+=653.

Workup

  1. customReaction
  2. customReaction
  3. stirringstirred at room temperature for 1 hour
  4. customReaction layers
  5. customwere partitioned
  6. washOrganic layer was washed successively with 1N hydrochloric acid and brine
  7. dry with materialOrganic was dried (magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2598effc0bb34fc4b7ba87c5b21c2b11
Source dataset
uspto-grants-2008_12
Patent number
US07470679B2

Reaction notes

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