Diisobutylaluminumhydride → 7-chloro-5-(2-chlorophenyl)-8-methoxy-3-methyl-1,2-dihydropyrazolo[3,4-b][1,4]benzodiazepine

HRID 2112531Notes

Reaction equation

HRID 2112531 reaction equation
NC1C=C(OC)C(Cl)=CC=1C(C1C=CC=CC=1Cl)=O.NC1C(C)=NN(CC=C)C=1Cl.[Cl:31][C:32]1[C:33]([O:57][CH3:58])=[CH:34][C:35]2[N:41]=[C:40]3[N:42](CC=C)[NH:43][C:44]([CH3:45])=[C:39]3[N:38]=[C:37]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=3[Cl:55])[C:36]=2[CH:56]=1.[H-].C([Al+]CC(C)C)C(C)C>>[Cl:31][C:32]1[C:33]([O:57][CH3:58])=[CH:34][C:35]2[N:41]=[C:40]3[NH:42][NH:43][C:44]([CH3:45])=[C:39]3[N:38]=[C:37]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=3[Cl:55])[C:36]=2[CH:56]=1

Participants

5

Reactant 4

HCID 21225700DiisobutylaluminumhydrideHCID 576423441-Allyl-5-chloro-3-methyl-1H-pyrazol-4-amineHCID 57642381(2-Amino-5-chloro-4-methoxyphenyl)-(2-chlorophenyl)-methanoneHCID 1784566427-chloro-5-(2-chlorophenyl)-8-methoxy-3-methyl-1-prop-2-enyl-2H-pyrazolo[3,4-b][1,4]benzodiazepine

Product 1

HCID 1784864227-chloro-5-(2-chlorophenyl)-8-methoxy-3-methyl-1,2-dihydropyrazolo[3,4-b][1,4]benzodiazepine

Procedure

7-chloro-5-(2-chlorophenyl)-1,2-dihydro-8-methoxy-3-methyl-pyrazolo[3,4-b][1,4]benzodiazepine (IVcc) was prepared by reacting 0.0023 moles of (2-amino-5-chloro-4-methoxyphenyl)-(2-chlorophenyl)-methanone (Xcc) with 4-amino-5-chloro-3-methyl-1-(2-propenyl)-1H-pyrazole (XIII), and subsequent dealkylation of the intermediate, 7-chloro-5-(2-chlorophenyl)-1,2-dihydro-8-methoxy-3-methyl-1-(2-propenyl)-pyrazolo[3,4-b][1,4]benzodiazepine (XIVcc) with diisobutylaluminum hydride in a manner analogous to Example 72. MH+/Z=373.

Sources & evidence

ORD record
ord-9c207f0b3f6442c7b37a9dd01bdd5dcc
Source dataset
uspto-grants-2009_04
Patent number
US07524840B2

Reaction notes

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