Hydrochloric Acid → HCID 67403490, compound

HRID 909863Notes

Reaction equation

HRID 909863 reaction equation
Cl.[N:2]1[C:8]2=[CH:9][CH2:10][S:11][C:7]2=[CH:6][CH:5]=[CH:4][N:3]=1.N1C(C)=CC(C)=CC=1C.NC(N)=[O:23]>C(Cl)Cl.C1COCC1>[O:23]=[C:6]1[C:7]2[S:11][CH:10]=[CH:9][C:8]=2[N:2]=[N:3][CH:4]=[CH:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 79532,4,6-TrimethylpyridineHCID 66708587HCID 66708587, compound

Product 1

HCID 67403490HCID 67403490, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The synthesis of I, J analogs of the benzodiazepines scaffold is illustrated in the following pathway. In both approaches chiral amino acid are introduced into the synthesis raising the diversity around the α carbon. Thieno diazepine I is prepared from 2-amino-3-acyl)-thiophenes 5, which reacts with pre formed Boc amino acid chloride (amino acid, BTC, collidine, THF or DCM). Deprotection of 8 (4N HCl) with concomitant ring closure leads to 2-oxothienodiazepine I. Thiophenodiazepine J can be prepared starting from 2-amino-3-carboxy-thiophenes A, which after pre activation to the thienooxzaine dione (BTC, collidine, THF or DCM)) reacts with amino ketone to obtain 9, ring closure afford 5-oxothienodiazepine.

Workup

  1. customto obtain 9, ring closure

Sources & evidence

ORD record
ord-c9c9a0ae18c94f1e953a2f65716487db
Source dataset
uspto-grants-2011_09
Patent number
US08019550B2

Reaction notes

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