Trifluoroacetic acid → (E)-4-(3-iodophenyl)-8-(2-phenylethynyl)-1H-benzo[b][1,4]diazepin-2(3H)-one

HRID 1062132Notes

Reaction equation

HRID 1062132 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][C:9]=1[NH:22][C:23](=[O:34])[CH2:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([I:33])[CH:28]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[I:33][C:29]1[CH:28]=[C:27]([C:25]2[CH2:24][C:23](=[O:34])[NH:22][C:9]3[CH:10]=[C:11]([C:14]#[C:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:12]=[CH:13][C:8]=3[N:7]=2)[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86587994HCID 86587994, compound

Product 1

HCID 22224695(E)-4-(3-iodophenyl)-8-(2-phenylethynyl)-1H-benzo[b][1,4]diazepin-2(3H)-oneYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from {2-[3-(3-iodo-phenyl)-3-oxo-propionylamino]-4-phenylethynyl-phenyl}-carbamic acid tert.-butyl ester (Example K7) (871 mg, 1.5 mmol) by treatment with TFA in CH2Cl2 according to the general procedure M. Obtained as a light yellow solid (542 mg).

Sources & evidence

ORD record
ord-f9a0dc961f0046758a30001596b03097
Source dataset
uspto-grants-2005_11
Patent number
US06960578B2

Reaction notes

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