HCID 18958928, compound → HCID 15233932, compound

HRID 1708475Notes

Reaction equation

HRID 1708475 reaction equation
[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:32]([C:33]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:31]=[N:30][N:29]=3)=[CH:18][CH:17]=2)[C:13](=[O:52])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:53]=[O:54])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].[CH2:55]([Mg]Br)[CH3:56]>O1CCCC1>[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:32]([C:33]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[N:31]=[N:30][N:29]=3)=[CH:20][CH:21]=2)[C:13](=[O:52])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:53]([OH:54])[CH2:55][CH3:56])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 18958928HCID 18958928, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 15233932HCID 15233932, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a suspension of 1.00 g of 2-Butyl-3,4-dihydro-4-oxo-3-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5yl][1,1'-biphenyl]-4-yl]methyl]-6-quinazolinecarboxaldehyde in 10 ml of tetrahydrofuran, cooled to -78° C. and 2.833 ml of a 1.0M solution of ethylmagnesium bromide rapidly added. The cooling bath is removed and the reaction mixture allowed to warm until a complete solution. The cooling bath is again applied and the reaction mixture cooled to -78° C. and stirred for 0.5 hours. The bath is removed and the reaction mixture allowed to reach room temperature. An aqueous solution of ammonium chloride is added and the reaction mixture extracted with ethyl acetate. The organic layer is dried and concentrated in vacuo to give 0.821 g of the desired product as a solid. FAB mass spec 737 (M+H).

Workup

  1. customThe cooling bath is removed
  2. temperatureto warm until a complete solution
  3. temperaturethe reaction mixture cooled to -78° C.
  4. customThe bath is removed
  5. customto reach room temperature
  6. additionAn aqueous solution of ammonium chloride is added
  7. extractionthe reaction mixture extracted with ethyl acetate
  8. customThe organic layer is dried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68a19861d53641fd838b60d08313b542
Source dataset
uspto-grants-1994_10
Patent number
US05358951

Reaction notes

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