Bromine → HCID 15511794, compound

HRID 2217278Notes

Reaction equation

HRID 2217278 reaction equation
O.[OH-].[Li+].[NH2:4][C:5]1[C:40]([Br:41])=[CH:39][C:8]([C:9]([C@@H:11]2[CH2:13][C@H:12]2[C:14]([N:16]2[CH2:21][CH2:20][CH:19]([N:22]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[C:28]([O:32][CH2:33][C:34]([O:36]C)=[O:35])[CH:29]=4)[NH:24][C:23]3=[O:38])[CH2:18][CH2:17]2)=[O:15])=[O:10])=[CH:7][C:6]=1[Br:42].[K+].[Br-].BrBr>O.C1COCC1.CO>[NH2:4][C:5]1[C:40]([Br:41])=[CH:39][C:8]([C:9]([C@@H:11]2[CH2:13][C@H:12]2[C:14]([N:16]2[CH2:21][CH2:20][CH:19]([N:22]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[C:28]([O:32][CH2:33][C:34]([OH:36])=[O:35])[CH:29]=4)[NH:24][C:23]3=[O:38])[CH2:18][CH2:17]2)=[O:15])=[O:10])=[CH:7][C:6]=1[Br:42]

Participants

8

Reactant 4

HCID 24408Bromine3×HCID 168937Lithium hydroxide, monohydrateHCID 253877Potassium BromideHCID 69310387HCID 69310387, compound

Product 1

HCID 15511794HCID 15511794, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.15 g (3.57 mmol) of lithium hydroxide hydrate in 10 mL of water was added to a solution of 0.6 g (0.903 mmol) of trans-3-{1-[2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]-4-piperidinyl}-3,4-dihydro-6-(methoxycarbonylmethoxy)-2(1H)-quinazolinone (Item No. 22) in a mixture of 10 mL of THF and 10 mL of methanol. After stirring for 14 hours at ambient temperature, the organic solvents were distilled off in vacuo and the residue remaining was combined with 3.6 mL of 1N hydrochloric acid. The precipitate formed was suction filtered and dried in vacuo at 30° C. The residue was taken up in tetrahydrofuran, the solution formed was filtered while hot and, after cooling, combined with diisopropyl ether until the precipitation reaction had ended. The precipitate was suction filtered. After drying in a circulating air drier 0.25 g (43% of theoretical) of colorless crystals were obtained. Rf 0.63 (MP C); IR (KBr): 1730 cm−1 (C═O); MS: ESI: (M−H+2Na)+=693/695/697 (Br2); (M−H)−: 647/649/651 (Br2); (M+Na)+: 671/673/675 (Br2).

Workup

  1. distillationthe organic solvents were distilled off in vacuo
  2. customThe precipitate formed
  3. filtrationfiltered
  4. customdried in vacuo at 30° C
  5. customthe solution formed
  6. filtrationwas filtered while hot and,
  7. temperatureafter cooling
  8. customcombined with diisopropyl ether until the precipitation reaction
  9. filtrationfiltered
  10. customAfter drying in a circulating air drier 0.25 g (43% of theoretical) of colorless crystals
  11. customwere obtained

Sources & evidence

ORD record
ord-cf313419780f4673add2333f7191b614
Source dataset
uspto-grants-2008_08
Patent number
US07407963B2

Reaction notes

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