o-Bis(bromomethyl)benzene → HCID 53888344, compound

HRID 1378004Notes

Reaction equation

HRID 1378004 reaction equation
[NH2:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=4[C:15](=[O:23])[N:14]4[CH2:24][CH2:25][C@H:13]4[C:12]=23)[N:4]=1.C(N(C(C)C)C(C)C)C.Br[CH2:36][C:37]1[C:38]([CH2:43]Br)=[CH:39][CH:40]=[CH:41][CH:42]=1>C(Cl)Cl>[Cl:22][C:21]1[C:16]2[C:15](=[O:23])[N:14]3[CH2:24][CH2:25][C@H:13]3[C:12]3[N:11]([CH:10]=[N:9][C:8]=3[C:5]3[N:4]=[C:3]([CH2:2][N:1]4[CH2:43][C:38]5[C:37](=[CH:42][CH:41]=[CH:40][CH:39]=5)[CH2:36]4)[O:7][N:6]=3)[C:17]=2[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 66665o-Bis(bromomethyl)benzeneHCID 81531DiisopropylethylamineHCID 54208158HCID 54208158, compound

Product 1

HCID 53888344HCID 53888344, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.56 g (10 mmol) of (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, 15 ml of methylene chloride, 8.6 ml (50 mmol) of N-ethyldiisopropylamine and 2.64 g (10 mmol) of α,α'-dibromo-o-xylene were stirred at room temperature for 20 hours. The reaction solution was washed three times with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on 500 g of silica gel while eluting with methylene chloride/methanol 19/1. There were obtained 1.55 g (33%) of (S)-8-chloro-12,12a-dihydro-1-(5-isoindolin-2-ylmethyl-1,2,4-oxadiazol-3-yl)-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, which was converted into the hydrochloride of m.p. 218°-222°.

Workup

  1. washThe reaction solution was washed three times with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customThe residue was chromatographed on 500 g of silica gel
  5. washwhile eluting with methylene chloride/methanol 19/1

Sources & evidence

ORD record
ord-76819ccfc404440a8a0955d6ab2f3617
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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